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Cyclic (Alkyl)(amino)carbenes (CAACs): Recent Developments

Journal Article · · Angewandte Chemie (International Edition)
 [1];  [2];  [2];  [2]
  1. Univ. of California, San Diego, La Jolla, CA (United States); DOE/OSTI
  2. Univ. of California, San Diego, La Jolla, CA (United States)
+ Show Author Affiliations

Discovered in 2005, cyclic (alkyl)(amino)carbenes (CAACs) are among the most nucleophilic (σ donating) and also electrophilic (π-accepting) stable carbenes known to date. These properties allow them to activate a variety of small molecules and enthalpically strong bonds, to stabilize highly reactive main-group and transition-metal diamagnetic and paramagnetic species, and to bind strongly to metal centers, which gives rise to very robust catalysts. The most important results published up to the end of 2013 are briefly summarized here, while the majority of this Review focuses on findings reported within the last three years.

Research Organization:
Univ. of California, San Diego, CA (United States)
Sponsoring Organization:
USDOE Office of Science (SC); National Science Foundation (NSF); SOLVAY Inc.
Grant/Contract Number:
SC0009376
OSTI ID:
1533103
Alternate ID(s):
OSTI ID: 1374470
Journal Information:
Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 34 Vol. 56; ISSN 1433-7851
Publisher:
WileyCopyright Statement
Country of Publication:
United States
Language:
English

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Low-Temperature N 2 Binding to Two-Coordinate L 2 Fe 0 Enables Reductive Trapping of L 2 FeN 2 − and NH 3 Generation journal November 2014
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C 4 Cumulene and the Corresponding Air-Stable Radical Cation and Dication journal March 2014
Isolation of a Neutral Boron-Containing Radical Stabilized by a Cyclic (Alkyl)(Amino)Carbene journal June 2014
A Cyclization-Rearrangement Cascade for the Synthesis of Structurally Complex Chiral Gold(I)-Aminocarbene Complexes journal July 2014
Diborabutatriene: An Electron-Deficient Cumulene journal May 2014
Two-Coordinate Fe 0 and Co 0 Complexes Supported by Cyclic (alkyl)(amino)carbenes journal June 2014
Cross-Coupling Reactions between Stable Carbenes journal May 2014
Trinuclear Gold Clusters Supported by Cyclic (alkyl)(amino)carbene Ligands: Mimics for Gold Heterogeneous Catalysts journal July 2014
(Aminocarbene)(Divinyltetramethyldisiloxane)Iron(0) Compounds: A Class of Low-Coordinate Iron(0) Reagents journal June 2014
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Low-Temperature N 2 Binding to Two-Coordinate L 2 Fe 0 Enables Reductive Trapping of L 2 FeN 2 − and NH 3 Generation journal November 2014
Cyclic Alkyl Amino Carbene (CAAC) Ruthenium Complexes as Remarkably Active Catalysts for Ethenolysis journal December 2014
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Air-Stable (CAAC)CuCl and (CAAC)CuBH 4 Complexes as Catalysts for the Hydrolytic Dehydrogenation of BH 3 NH 3 journal March 2015
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A Triatomic Silicon(0) Cluster Stabilized by a Cyclic Alkyl(amino) Carbene journal January 2016
Double Deprotonation of Pyridinols Generates Potent Organic Electron-Donor Initiators for Haloarene-Arene Coupling journal March 2016
Mild and Complete Carbonyl Ligand Scission on a Mononuclear Transition Metal Complex journal March 2016
Z -Selective (Cross-)Dimerization of Terminal Alkynes Catalyzed by an Iron Complex journal April 2016
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Cooperative Catalysis and Activation with N-Heterocyclic Carbenes journal October 2016
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A Two-Coordinate Cyclic (Alkyl)(amino)silylene: Balancing Thermal Stability and Reactivity journal November 2016
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Elusive Antimony-Centered Radical Cations: Isolation, Characterization, Crystal Structures, and Reactivity Studies journal December 2016
Stable Di- and Tri-coordinated Carbon(II) Supported by an Electron-Rich β-Diketiminate Ligand journal December 2016
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Persistent and Stable Radicals of the Heavier Main Group Elements and Related Species journal March 2003
P 4 Activation by Main Group Elements and Compounds journal July 2010
Organic Mixed Valence journal August 2011
Diradicals journal July 2013
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The Medicinal Applications of Imidazolium Carbene−Metal Complexes journal August 2009
Carbenes Introduction journal August 2009
P 4 Activation by Late-Transition Metal Complexes † ‡ journal July 2010
Early-Transition-Metal-Mediated Activation and Transformation of White Phosphorus journal July 2010
Stable Carbenes journal January 2000
π-Bonding and the Lone Pair Effect in Multiple Bonds between Heavier Main Group Elements journal December 1999
Carbene Stabilization of Highly Reactive Main-Group Molecules journal December 2011
A stable crystalline carbene journal January 1991
Methyleneoxirane-cyclopropanone and related rearrangements in C3H4O cation radicals and neutral molecules. A quest for the oxyallyl intermediate journal July 1991
Synthesis and x-ray crystal structure of [(iso-Pr2N)2P(H)CP(N-iso-Pr2)2]+CF3SO3-: a carbene, a cumulene, or a phosphaacetylene? journal December 1992
Ge2H2: a germanium-containing molecule with a low-lying monobridged equilibrium geometry journal July 1993
A stable diaminocarbene journal November 1995
Analogous .alpha.,.alpha.'-bis-carbenoid, triply bonded species: synthesis of a stable .lambda.3-phosphino carbene-.lambda.5-phosphaacetylene journal September 1988
Theoretical study of the relative stabilities of C2H2 and Si2H2 conformers journal February 1984
Binuclear complexes of ruthenium ammines journal February 1973
Direct approach to measuring the Franck-Condon barrier to electron transfer between metal ions journal July 1969
On the Mechanism of Thiamine Action. IV. 1 Evidence from Studies on Model Systems journal July 1958
The Addition of Dichlorocarbene to Olefins journal December 1954
Stable (Amino)(phosphino)carbenes:  Difunctional Molecules journal June 2002
Constructing a Stable Carbene with a Novel Topology and Electronic Framework journal November 2003
Rearrangement of a 2-Methylenecyclobutanone Derivative Triggered by Photoinduced Electron Transfer:  An Unprecedented Oxa Analogue of the Tetramethyleneethane Radical Cation journal January 2004
Mono- and Diaminocarbenes from Chloroiminium and -amidinium Salts:  Synthesis of Metal-Free Bis(dimethylamino)carbene journal February 2004
Synthesis, Reactivity, and Ligand Properties of a Stable Alkyl Carbene journal July 2004
A Stable N-Heterocyclic Carbene with a Diboron Backbone journal March 2005
Persistent (Amino)(Silyl)Carbenes journal May 2005
Stable Planar Six-π-Electron Six-Membered N-Heterocyclic Carbenes with Tunable Electronic Properties journal July 2005
Effective Modulation of the Donor Properties of N-Heterocyclic Carbene Ligands by “Through-Space” Communication within a Planar Chiral Scaffold journal October 2007
NHC-Mediated Aggregation of P 4 :  Isolation of a P 12 Cluster journal November 2007
A Crystalline Phosphinyl Radical Cation journal August 2010
A Viable Anionic N-Heterocyclic Dicarbene journal October 2010
Carbene-Stabilized Beryllium Borohydride journal June 2012
Catalytic Dehydrogenative Borylation of Terminal Alkynes by a SiNN Pincer Complex of Iridium journal February 2013
Overturning Established Chemoselectivities: Selective Reduction of Arenes over Malonates and Cyanoacetates by Photoactivated Organic Electron Donors journal July 2013
Formation of a 1,4-Diamino-2,3-disila-1,3-butadiene Derivative journal October 2013
Bottleable (Amino)(Carboxy) Radicals Derived from Cyclic (Alkyl)(Amino) Carbenes journal December 2013
Stabilization of a Cobalt–Cobalt Bond by Two Cyclic Alkyl Amino Carbenes journal January 2014
Comparative Reactivity of Different Types of Stable Cyclic and Acyclic Mono- and Diamino Carbenes with Simple Organic Substrates journal March 2014
Catalytic Anti-Markovnikov Hydrobromination of Alkynes journal June 2014
Electronic Structure and Slow Magnetic Relaxation of Low-Coordinate Cyclic Alkyl(amino) Carbene Stabilized Iron(I) Complexes journal August 2014
One-Electron-Mediated Rearrangements of 2,3-Disiladicarbene journal June 2014
Cyclic Alkyl(amino) Carbene Stabilized Biradical of Disilicontetrachloride journal June 2014
Gold-Catalyzed Hydroarylation of Alkenes with Dialkylanilines journal September 2014
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Electron-Induced Conversion of Silylones to Six-Membered Cyclic Silylenes journal November 2014
Experimental Assessment of the Strengths of B–B Triple Bonds journal January 2015
Carbene-Dichlorosilylene Stabilized Phosphinidenes Exhibiting Strong Intramolecular Charge Transfer Transition journal December 2014
A Stable Anionic N-Heterocyclic Carbene and Its Zwitterionic Complexes journal August 2008
Carbene-Stabilized Diphosphorus journal October 2008
Synthesis of a Simplified Version of Stable Bulky and Rigid Cyclic (Alkyl)(amino)carbenes, and Catalytic Activity of the Ensuing Gold(I) Complex in the Three-Component Preparation of 1,2-Dihydroquinoline Derivatives journal June 2009
An N , N ′-Diamidocarbene: Studies in C−H Insertion, Reversible Carbonylation, and Transition-Metal Coordination Chemistry journal November 2009
Stable Aminooxy- and Aminothiocarbenes journal November 1998
Olefin Metathesis-Active Ruthenium Complexes Bearing a Nucleophilic Carbene Ligand journal March 1999
Stable Radicals from Commonly Used Precursors Trichlorosilane and Diphenylchlorophosphine journal April 2015
Carbene Supported Dimer of Heavier Ketenimine Analogue with P and Si Atoms journal May 2015
Air-Persistent Monomeric (Amino)(carboxy) Radicals Derived from Cyclic (Alkyl)(Amino) Carbenes journal June 2015
Highly Selective Hydrogenation of Aromatic Ketones and Phenols Enabled by Cyclic (Amino)(alkyl)carbene Rhodium Complexes journal July 2015
Three-Coordinate Iron(IV) Bisimido Complexes with Aminocarbene Ligation: Synthesis, Structure, and Reactivity journal October 2015
The Janus Face of the X Ligand in the Copper-Catalyzed Azide–Alkyne Cycloaddition journal December 2015
Singlet (Phosphino)phosphinidenes are Electrophilic journal June 2016
Reactions of Persistent Carbenes with Hydrogen-Terminated Silicon Surfaces journal June 2016
Synthesis of Hemilabile Cyclic (Alkyl)(amino)carbenes (CAACs) and Applications in Organometallic Chemistry journal June 2016
The Structure of the Carbene Stabilized Si 2 H 2 May Be Equally Well Described with Coordinate Bonds as with Classical Double Bonds journal August 2016
Transition-Metal-like Behavior of Main Group Elements: Ligand Exchange at a Phosphinidene journal December 2016
Main-Group Metallomimetics: Transition Metal-like Photolytic CO Substitution at Boron journal January 2017
Transient Azomethine-ylides from a Stable Amino-carbene and an Aldiminium Salt journal February 2003
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Abnormal C5-Bound N-Heterocyclic Carbenes:  Extremely Strong Electron Donor Ligands and Their Iridium(I) and Iridium(III) Complexes journal May 2004
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A Brief Survey of Our Contribution to Stable Carbene Chemistry journal October 2011
Tuning the Electronic Properties of Carbenes: A Systematic Comparison of Neighboring Amino versus Amido Groups journal March 2012
Saturated Abnormal NHC–Gold(I) Complexes: Synthesis and Catalytic Activity journal March 2013
Determining the π-Acceptor Properties of N-Heterocyclic Carbenes by Measuring the 77 Se NMR Chemical Shifts of Their Selenium Adducts journal September 2013
Boron–Boron Multiple Bonding: From Charged to Neutral and Back Again journal November 2014
Gold(I) and Gold(III) Complexes of Cyclic (Alkyl)(amino)carbenes journal November 2014
Kinetic Selectivity of Olefin Metathesis Catalysts Bearing Cyclic (Alkyl)(Amino)Carbenes journal February 2008
Determination of N-Heterocyclic Carbene (NHC) Steric and Electronic Parameters using the [(NHC)Ir(CO) 2 Cl] System journal January 2008
Novel Expanded Ring N-Heterocyclic Carbenes: Free Carbenes, Silver Complexes, And Structures journal July 2008
Donor Properties of a Series of Two-Electron Ligands journal February 2009
Facile Synthesis of Silver(I)−Carbene Complexes. Useful Carbene Transfer Agents journal March 1998
Peculiar boron startles again journal June 2015
Main-group elements as transition metals journal January 2010
An overview of N-heterocyclic carbenes journal June 2014
Multiple complexation of CO and related ligands to a main-group element journal June 2015
Metal-free binding and coupling of carbon monoxide at a boron–boron triple bond journal October 2013
Neutral zero-valent s-block complexes with strong multiple bonding journal June 2016
Isolation of crystalline carbene-stabilized P2-radical cations and P2-dications journal April 2010
Stable singlet carbenes as mimics for transition metal centers journal January 2011
Carbene-stabilized main group diatomic allotropes journal January 2012
Phosphaalkene vs. phosphinidene: the nature of the P–C bond in carbonyl-decorated carbene → PPh adducts journal January 2014
Evolution of neutral organic super-electron-donors and their applications journal January 2014
N-heterocyclic carbene metal complexes: photoluminescence and applications journal January 2014
An efficient synthetic route to stable bis(carbene)borylenes [(L 1 )(L 2 )BH] journal January 2014
Current advances in fused tetrathiafulvalene donor–acceptor systems journal January 2015
Singlet carbenes as mimics for transition metals: synthesis of an air stable organic mixed valence compound [M 2 (C 2 ) + ˙; M = cyclic(alkyl)(amino)carbene] journal January 2014
Ancillary ligand-free copper catalysed hydrohydrazination of terminal alkynes with NH 2 NH 2 journal January 2016
Silicon based radicals, radical ions, diradicals and diradicaloids journal January 2016
Donor–acceptor bonding in novel low-coordinated compounds of boron and group-14 atoms C–Sn journal January 2016
Group 1 and 2 cyclic (alkyl)(amino)carbene complexes journal January 2015
Monomeric siliconthiodichloride trapped by a Lewis base journal January 2015
25 years of N-heterocyclic carbenes: activation of both main-group element–element bonds and NHCs themselves journal January 2016
Catalytic dehydrogenative borylation of terminal alkynes by POCOP-supported palladium complexes journal January 2015
Diverse reactivity of a tricoordinate organoboron L 2 PhB: (L = oxazol-2-ylidene) towards alkali metal, group 9 metal, and coinage metal precursors journal January 2015
A soluble molecular variant of the semiconducting silicondiselenide journal January 2015
Ligand survey results in identification of PNP pincer complexes of iridium as long-lived and chemoselective catalysts for dehydrogenative borylation of terminal alkynes journal January 2015
Isolation of cationic and neutral (allenylidene)(carbene) and bis(allenylidene)gold complexes journal January 2016
Isolation of Au-, Co-η 1 PCO and Cu-η 2 PCO complexes, conversion of an Ir–η 1 PCO complex into a dimetalladiphosphene, and an interaction-free PCO anion journal January 2016
A cyclic (alkyl)(amido)carbene: synthesis, study and utility as a desulfurization reagent journal January 2016
Highly photoluminescent copper carbene complexes based on prompt rather than delayed fluorescence journal January 2016
Aza-Morita–Baylis–Hillman reactions catalyzed by a cyclopropenylidene journal January 2016
Reduction of a diamidocarbene-supported borenium cation: isolation of a neutral boryl-substituted radical and a carbene-stabilized aminoborylene journal January 2016
Copper-catalyzed dehydrogenative borylation of terminal alkynes with pinacolborane journal January 2017
Electron transfer properties of active aldehydes derived from thiamin coenzyme analogues journal January 1997
Tetrathiafulvalenes as building blocks in supramolecular chemistry II journal January 2000
Complexation of stable carbenes with alkali metals journal January 1999
Electrochemical reduction of an imidazolium cation: a convenient preparation of imidazol-2-ylidenes and their observation in an ionic liquid journal January 2004
A stable chiral diaminocyclopropenylidene journal January 2007
Tetrathiafulvalene (TTF) derivatives: key building-blocks for switchable processes journal January 2009
Beyond catalysis: N-heterocyclic carbene complexes as components for medicinal, luminescent, and functional materials applications journal January 2010
Synthesis and isolation of a stable, axially-chiral seven-membered N-heterocyclic carbene journal January 2009
Imidazol-2-ylidene-4-olate: an anionic N-heterocyclic carbene pre-programmed for further derivatization journal January 2009
Advances in selective activation and application of ammonia in homogeneous catalysis journal January 2010
Click chemistry: function follows form journal January 2010
Ammonia N–H activation by a N,N′-diamidocarbene journal January 2010
Simple and versatile synthesis of copper and silver N-heterocyclic carbene complexes in water or organic solvents journal January 2010
N-Heterocyclic carbenes versus transition metals for stabilizing phosphinyl radicals journal January 2011
Organocatalytic umpolung: N-heterocyclic carbenes and beyond journal January 2012
Reaction of pentaarylboroles with carbon monoxide: an isolable organoboron carbonyl complex journal January 2012
The structure of singlet carbene molecules journal January 1980
Exploring the reactivity of white phosphorus with electrophilic carbenes: synthesis of a P4 cage and P8 clusters journal January 2013
Neutral tricoordinated beryllium(0) compounds – isostructural to BH3 but isoelectronic to NH3 journal January 2013
Beryllium chemistry the safe way: a theoretical evaluation of low oxidation state beryllium compounds journal January 2013
Ligand mediated iron catalyzed dimerization of terminal aryl alkynes: scope and limitations journal January 2014
Carbene-stabilized main group radicals and radical ions journal January 2013
Reductive generation of stable, five-membered N,N′-diamidocarbenes journal January 2014
Infrared spectroscopic studies of hydrogenated silicon clusters: Guiding the search for Si journal March 2005
Stable Carbenes: From ‘Laboratory Curiosities' to Catalysis Mainstays journal June 2013
Copper-Catalyzed Hydrofunctionalization of Alkynes journal March 2016
Computational study of Si2H and Si2H2 species as candidates of interstellar molecules
  • Osamura, Yoshihiro; Kaiser, Ralf I.
  • ASTROCHEMISTRY: From Laboratory Studies to Astronomical Observations, AIP Conference Proceedings https://doi.org/10.1063/1.2359567
conference January 2006
Stable four- -electron, four-membered heterocyclic cations and carbenes journal September 2006
Allene formation by gold catalyzed cross-coupling of masked carbenes and vinylidenes journal August 2007
Isolation of bis(copper) key intermediates in Cu-catalyzed azide-alkyne “click reaction” journal June 2015
Synthesis of Carbenes Through Substitution Reactions at a Carbene Center journal August 2003
Cyclopropenylidenes: From Interstellar Space to an Isolated Derivative in the Laboratory journal May 2006
Facile Splitting of Hydrogen and Ammonia by Nucleophilic Activation at a Single Carbon Center journal April 2007
A Stable Silicon(0) Compound with a Si=Si Double Bond journal August 2008
CHEMISTRY: Soluble Allotropes of Main-Group Elements journal August 2008
Isolation of a C5-Deprotonated Imidazolium, a Crystalline "Abnormal" N-Heterocyclic Carbene journal October 2009
Synthesis and Characterization of a Neutral Tricoordinate Organoboron Isoelectronic with Amines journal July 2011
Ambient-Temperature Isolation of a Compound with a Boron-Boron Triple Bond journal June 2012
Direct Evidence of a Dinuclear Copper Intermediate in Cu(I)-Catalyzed Azide-Alkyne Cycloadditions journal April 2013
Editors' Choice journal January 2015
Stable Versions of Transient Push-Pull Carbenes: Extending Lifetimes from Nanoseconds to Weeks journal May 2000
(Amino)(Aryl)Carbenes: Stable Singlet Carbenes Featuring a Spectator Substituent journal June 2001
Differenzelektronendichte im gefalteten 2 π-aromatischen System eines 1,3-Dihydro-1,3-diborets / Difference Electron Density in a Folded 2π-Aromatic System of a 1,3-Dihydro-1,3-diborete journal December 1991
Isolation of a Cyclic (Alkyl)(amino)germylene journal July 2016
Direct estimate of the internal π-donation to the carbene centre within N-heterocyclic carbenes and related molecules journal January 2015
Hybrid super electron donors – preparation and reactivity journal January 2012

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N-Heterocyclic Carbene Analogues of Thiele and Chichibabin Hydrocarbons journal April 2018
CO 2 -Fixierung und Spaltung durch unpolare Mehrfachbindungen journal April 2018
Transition-Metal-Like Behavior of Monovalent Boron Compounds: Reduction, Migration, and Complete Cleavage of CO at a Boron Center journal April 2018
Silanylidene and Germanylidene Anions: Valence-Isoelectronic Species to the Well-Studied Phosphinidene journal August 2018
Formazanate Complexes of Hypervalent Group 14 Elements as Precursors to Electronically Stabilized Radicals journal June 2018
Observation of Carbodicarbene Ligand Redox Noninnocence in Highly Oxidized Iron Complexes journal November 2018
Einfacher Zugang zum ersten stabilen {BH 2 } − Dihydroborylanion journal October 2018
Hydrierung borylierter Aromaten journal December 2018
Die selektive Arenhydrierung bietet einen direkten Zugang zu gesättigten Carbo‐ und Heterocyclen journal April 2019
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A Redox‐Confused Bismuth(I/III) Triamide with a T‐Shaped Planar Ground State journal May 2019
NHC‐Coordinated Diphosphene‐Stabilized Gold(I) Hydride and Its Reversible Conversion to Gold(I) Formate with CO 2 journal September 2019
Reactivity of a Dihydrodiborene with CO: Coordination, Insertion, Cleavage, and Spontaneous Formation of a Cyclic Alkyne journal October 2017
Mono‐ and Bis(imidazolidinium ethynyl) Cations and Reduction of the Latter To Give an Extended Bis‐1,4‐([3]Cumulene)‐ p ‐carboquinoid System journal January 2018
N-Heterocyclic Carbene Analogues of Thiele and Chichibabin Hydrocarbons journal April 2018
CO 2 Binding and Splitting by Boron-Boron Multiple Bonds journal April 2018
Engineering the Frontier Orbitals of a Diazadiborinine for Facile Activation of H 2 , NH 3 , and an Isonitrile journal May 2018
Coumaraz-2-on-4-ylidene: Ambiphilic N-Heterocyclic Carbenes with a Tunable Electronic Structure journal June 2018
Carbenes and Nitrenes: Recent Developments in Fundamental Chemistry journal August 2018
Stable Diporphyrinylaminyl Radical and Nitrenium Ion journal June 2018
An Isolable Terminal Imido Complex of Palladium and Catalytic Implications journal December 2018
Observation of Carbodicarbene Ligand Redox Noninnocence in Highly Oxidized Iron Complexes journal November 2018
Facile Synthesis of a Stable Dihydroboryl {BH 2 } − Anion journal November 2018
Hydrogenation of Borylated Arenes journal May 2019
Borane-Catalyzed Cross-Metathesis Strategy for Facile Transformation of Cyclic (Alkyl)(Amino)Germylenes journal December 2018
Facile Cleavage of the P=P Double Bond in Vinyl-Substituted Diphosphenes journal December 2018
A New Class of Neutral Boron-Based Diradicals Spanned by a Two-Carbon-Atom Bridge journal January 2019
Azo‐MICs: Redox‐Active Mesoionic Carbene Ligands Derived from Azoimidazolium Dyes journal January 2019
Phosphine‐Stabilized Diiododiborenes: Isolable Diborenes with Six Labile Bonds journal March 2019
Selective Arene Hydrogenation for Direct Access to Saturated Carbo- and Heterocycles journal April 2019
A Redox‐Confused Bismuth(I/III) Triamide with a T‐Shaped Planar Ground State journal June 2019
Persistent Borafluorene Radicals journal February 2020
Yellow Circularly Polarized Luminescence from C 1 ‐Symmetrical Copper(I) Complexes journal November 2019
Palladacycles bearing COOH-/ester-functionalized N-heterocyclic carbenes: Divergent syntheses and catalytic applications: Palladacycles of Functionalized N-Heterocyclic Carbenes journal January 2019
Comprehensive Basicity Scales for N‐Heterocyclic Carbenes in DMSO: Implications on the Stabilities of N‐Heterocyclic Carbene and CO 2 Adducts journal December 2019
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Electronic and Ligand Properties of Skeletally Substituted Cyclic (Alkyl)(Amino)Carbenes (CAACs) and Their Reactivity towards Small Molecule Activation: A Theoretical Study journal July 2017
Coordination Behavior of a Planar Chiral Cyclic (Amino)(Ferrocenyl)Carbene Ligand in Iridium Complexes journal September 2017
Mono- and Dicoordinate Germanium(0) as a Four-Electron Donor journal January 2018
Cobaltocenylidene: A Mesoionic Metalloceno Carbene, Stabilized in a Gold(III) Complex journal February 2018
Zinc-Containing Radical Anions via Single Electron Transfer to Donor-Acceptor Adducts journal February 2018
Carbene-Stabilized Exceptional Silicon Halides journal November 2018
Visible-Light Catalytic Photooxygenation of Monoterpene Indole Alkaloids: Access to Spirooxindole-1,3-oxazines journal June 2018
Intercepting a Transient Phosphino‐Arsinidene journal June 2018
Neutral, Cationic and Hydride-substituted Siloxygermylenes journal September 2018
Planar‐Chiral Ferrocene‐Based N‐Heterocyclic Carbene Ligands journal November 2018
London Dispersion Interactions in Pnictogen Cations [ECl 2 ] + and [E=E] 2+ (E=P, As, Sb) Supported by Anionic N ‐Heterocyclic Carbenes journal December 2018
Synthesis of Cyclic Alkyl(amino) Carbene Stabilized Silylenes with Small N‐Donating Substituents journal December 2018
Stable and Persistent Acyclic Diaminocarbenes with Cycloalkyl Substituents and Their Transformation to β-Lactams by Uncatalysed Carbonylation with CO journal December 2018
Metal‐Free Electrochemical Reduction of Carbon Dioxide Mediated by Cyclic(Alkyl)(Amino) Carbenes journal February 2019
Isolation of Cyclic(Alkyl)(Amino) Carbene–Bismuthinidene Mediated by a Beryllium(0) Complex journal February 2019
Cyclic(Alkyl)(Amino)Carbene (CAAC)‐Supported Zn Alkyls: Synthesis, Structure and Reactivity in Hydrosilylation Catalysis journal May 2019
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Intramolecular Ring‐Expansion Reaction (RER) and Intermolecular Coordination of In Situ Generated Cyclic (Amino)(aryl)carbenes (cAArCs) journal August 2019
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Benchmark study of popular density functionals for calculating binding energies of three-center two-electron bonds journal December 2018
The 13 C chemical shift and the anisotropy effect of the carbene electron-deficient centre: Simple means to characterize the electron distribution of carbenes journal January 2020
Saturated NHC Derived Dichalcogen Dications journal June 2020
From stable Sb- and Bi-centered radicals to a compound with a Ga=Sb double bond journal January 2018
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Cyclic amino(carboranyl) silylene: synthesis, structure and reactivity journal January 2018
An imine–gallium Lewis pair stabilized oxophosphinidene via an unexpected phosphirene rearrangement journal January 2018
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Experimental and quantum chemical studies of anionic analogues of N-heterocyclic carbenes journal January 2018
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Imino-stabilised phosphinidene (or azaphosphole?) and some of its derivatives journal January 2018
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The serendipitous discovery of a readily available redox-bistable molecule derived from cyclic(alkyl)(amino)carbenes journal January 2018
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Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
carbenes
chemistry
cyclic (alkyl)(amino)carbenes - (CAACs)
homogeneouscatalysis
transition metals