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Ligand–Metal Cooperation Enables Net Ring-Opening C–C Activation/Difunctionalization of Cyclopropyl Ketones

Journal Article · · ACS Catalysis
Not provided.
Research Organization:
Univ. of Wisconsin, Madison, WI (United States)
Sponsoring Organization:
USDOE Office of Science (SC)
DOE Contract Number:
SC0021021
OSTI ID:
2421697
Journal Information:
ACS Catalysis, Journal Name: ACS Catalysis Journal Issue: 17 Vol. 13; ISSN 2155-5435
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English

References (137)

Pyridine(diimine) Iron Diene Complexes Relevant to Catalytic [2+2]‐Cycloaddition Reactions journal December 2019
Position specific α-tert-alkylation of ketones journal January 1979
Dimerization of Cyclopropyl Ketones and Crossed Reactions of Cyclopropyl Ketones with Enones as an Entry to Five-Membered Rings journal March 2006
Ligand Redox Effects in the Synthesis, Electronic Structure, and Reactivity of an Alkyl−Alkyl Cross-Coupling Catalyst journal October 2006
Allylbarium Reagents: Unprecedented Regio- and Stereoselective Allylation Reactions of Carbonyl Compounds journal July 1994
Oxidation of Silyl Enol Ethers by Using IBX and IBX⋅N-Oxide Complexes: A Mild and Selective Reaction for the Synthesis of Enones journal March 2002
Auto‐Tandem Catalysis: Activation of Multiple, Mechanistically Distinct Process by a Single Catalyst journal August 2016
Transition metal-catalyzed carbon–carbon bond activation journal January 2004
“Cut and Sew” Transformations via Transition-Metal-Catalyzed Carbon–Carbon Bond Activation journal January 2017
Creating Stereocenters within Acyclic Systems by C–C Bond Cleavage of Cyclopropanes journal July 2020
Isocratic nonaqueous reversed-phase liquid chromatography of carotenoids journal February 1983
Enantioselective Desymmetrization of Cyclopropenes by Hydroacylation journal October 2010
Synthesis of the Tricyclic Core of Colchicine via a Dienyne Tandem Ring-Closing Metathesis Reaction journal May 2007
Visible‐Light‐Induced Ring‐Opening of Hydrogenolysis Spirocyclopropyl Oxindoles Through Photoredox Catalysis journal June 2019
Recent advances in asymmetric total synthesis of prostaglandins journal January 2017
Nickel-catalyzed cross coupling of non-activated alkyl halides: a mechanistic perspective journal January 2011
Analysis of key steps in the catalytic cross-coupling of alkyl electrophiles under Negishi-like conditions journal January 2005
Nickel-Catalyzed Defluorinative Coupling of Aliphatic Aldehydes with Trifluoromethyl Alkenes journal February 2022
SmI2-catalysed cyclization cascades by radical relay journal January 2019
Pd‐Catalyzed α‐Arylation of Trimethylsilyl Enol Ethers with Aryl Bromides and Chlorides: A Synergistic Effect of Two Metal Fluorides as Additives journal August 2006
Nickel-catalysed Negishi cross-coupling reactions: scope and mechanisms journal January 2009
The use of silyl enol ethers in the alkylation of substituted cyclanones journal January 1994
Properties of R3SiX Compounds and R3Si+ Ions: Do Silylium Ions Exist in Solution? journal July 1995
Asymmetric [3+2] Photocycloadditions of Cyclopropanes with Alkenes or Alkynes through Visible‐Light Excitation of Catalyst‐Bound Substrates journal April 2018
Metal Insertion into C−C Bonds in Solution journal April 1999
Total Synthesis of (−)-(α)-Kainic Acid via a Diastereoselective Intramolecular [3 + 2] Cycloaddition Reaction of an Aryl Cyclopropyl Ketone with an Alkyne journal May 2012
Nickel-Catalyzed Reductive Coupling of γ-Metalated Ketones with Unactivated Alkyl Bromides journal May 2022
Conversion constants for redox potentials measured versus different reference electrodes in acetonitrile solutions at 25°C journal January 2000
Nickel-Catalyzed Cross-Coupling of Photoredox-Generated Radicals: Uncovering a General Manifold for Stereoconvergence in Nickel-Catalyzed Cross-Couplings journal April 2015
Palladium-Catalyzed Regiocontrolled α-Arylation of Trimethylsilyl Enol Ethers with Aryl Halides journal November 2006
A new Synthesis of Cyclopropanes from Olefins journal October 1958
Palladium-Catalyzed Conjugate Allylation Reactions of α,β-Unsaturated N-Acylpyrroles journal October 2008
Mono- and bis(ethyne)nickel(0) complexes journal July 1989
[3+2] Cycloadditions of Aryl Cyclopropyl Ketones by Visible Light Photocatalysis journal January 2011
Recent Advances in Photoredox‐Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction journal July 2021
Protein Interactions in the Human Methionine Synthase−Methionine Synthase Reductase Complex and Implications for the Mechanism of Enzyme Reactivation journal June 2007
Tunable and Practical Homogeneous Organic Reductants for Cross-Electrophile Coupling journal November 2021
Total Synthesis of (±)-Taiwaniaquinol B via a Domino Intramolecular Friedel−Crafts Acylation/Carbonyl α-tert-Alkylation Reaction journal August 2005
Synthesis, Properties, and Reactivity with Carbon Dioxide of (allyl)2Ni(L) Complexes journal May 2011
Catalytic C–C Bond Activations via Oxidative Addition to Transition Metals journal June 2015
Distal γ‐C(sp3)−H Olefination of Ketone Derivatives and Free Carboxylic Acids journal June 2020
Ligand-Enabled γ-C(sp3)–H Activation of Ketones journal February 2018
Synthetic methods and reactions. 62. Transformations with chlorotrimethylsilane/sodium iodide, a convenient in situ iodotrimethylsilane reagent journal April 1979
Divergent Synthesis of Novel Cylindrocyclophanes that Inhibit Methicillin‐Resistant Staphylococcus aureus (MRSA) journal June 2020
Allylation Reactions by Using Allylstannanes in the Presence of a Lewis acid journal August 1979
Complementary regioselective cyclopropyl ring openings of 6-formyl-spirobicyclo[5.2]octane mediated by TMSCl and TBAI journal December 1997
Enantioselective Reactions of Donor/Acceptor Carbenoids Derived from α-Aryl-α-Diazoketones journal January 2009
Catalysis with Diboron(4)/Pyridine: Application to the Broad-Scope [3 + 2] Cycloaddition of Cyclopropanes and Alkenes journal May 2022
Asymmetric Ni-Catalyzed Conjugate Allylation of Activated Enones journal March 2008
Selective Intermolecular Oxidative Cross-Coupling of Enolates journal August 2015
Synthesis and Reactivity of Six‐Membered Oxa‐Nickelacycles: A Ring‐Opening Reaction of Cyclopropyl Ketones journal September 2009
Enolate formation from cyclopropyl ketones via iodide-induced ring opening and its use for stereoselective aldol reaction journal February 2001
Synthesis of prostaglandin D1 and D2 via the three-component coupling process journal January 1984
Access to Functionalized Quaternary Stereocenters via the Copper-Catalyzed Conjugate Addition of Monoorganozinc Bromide Reagents Enabled by N,N-Dimethylacetamide journal October 2018
Solvent dynamical effects in electron transfer: evaluation of electronic matrix coupling elements for metallocene self-exchange reactions journal July 1989
Intramolecular Condensation via an o-Quinone Methide: Total Synthesis of (±)-Heliol journal May 2012
Stereocontrolled organocatalytic synthesis of prostaglandin PGF2α in seven steps journal August 2012
Regioselective Ring-opening of Cyclopropyl Ketones with Organometallic Reagents journal November 1997
Transition Metal Catalyzed Enantioselective α-Heterofunctionalization of Carbonyl Compounds journal March 2011
New methodology for conjugate additions of allylic ligands to .alpha.,.beta.-unsaturated ketones: synthetic and spectroscopic studies journal May 1990
Visible-light-induced triple catalysis for a ring-opening cyanation of cyclopropyl ketones journal January 2020
Controlled Single-Electron Transfer via Metal–Ligand Cooperativity Drives Divergent Nickel-Electrocatalyzed Radical Pathways journal April 2021
Prostaglandin synthesis. 16. The three-component coupling synthesis of prostaglandins journal July 1988
[3+2] Cycloaddition Reaction of Cyclopropyl Ketones with Alkynes Catalyzed by Nickel/Dimethylaluminum Chloride journal October 2011
Rh(III)-Catalyzed C–H Activation-Initiated Directed Cyclopropanation of Allylic Alcohols journal April 2019
Homogeneous Organic Electron Donors in Nickel-Catalyzed Reductive Transformations journal June 2022
Soft Enolization of 3-Substituted Cycloalkanones Exhibits Significantly Improved Regiocontrol vs Hard Enolization Conditions journal December 2021
Ring opening of cyclopropyl ketones by trimethylsilyl iodide journal May 1981
General Paradigm in Photoredox Nickel‐Catalyzed Cross‐Coupling Allows for Light‐Free Access to Reactivity journal April 2020
Nickel-Catalyzed Borylation of Aryl Cyclopropyl Ketones with Bis(pinacolato)diboron to Synthesize 4-Oxoalkylboronates journal March 2009
Nickel-Catalyzed Decarboxylative Coupling of Redox-Active Esters with Aliphatic Aldehydes journal December 2021
Asymmetric Hetero‐Ene Reactions of Trimethylsilyl Enol Ethers Catalyzed by Tridentate Schiff Base Chromium(III) Complexes journal October 2003
Reversed redox generation of silyl radicals in a four-electrode flow-through EPR spectroelectrochemical cell journal January 2009
Generation of Organotantalum Reagents and Conjugate Addition to Enones journal April 2002
Pd(II)-Catalyzed Enantioselective C–H Activation of Cyclopropanes journal November 2011
Catalytic, Enantioselective Addition of Alkyl Radicals to Alkenes via Visible-Light-Activated Photoredox Catalysis with a Chiral Rhodium Complex journal May 2016
Enantioselective Photocatalytic [3 + 2] Cycloadditions of Aryl Cyclopropyl Ketones journal March 2016
Practical Conversion of Chlorosilanes into Alkoxysilanes without Generating HCl journal September 2011
Nonhydrolytic Synthesis of Branched Alkoxysiloxane Oligomers Si[OSiH(OR)2]4 (R=Me, Et) journal June 2010
Direct Silyl–Heck Reaction of Chlorosilanes journal April 2018
The Mukaiyama Aldol Reaction: 40 Years of Continuous Development journal July 2013
Formation of Nickeladihydropyran by Oxidative Addition of Cyclopropyl Ketone. Key Intermediate in Nickel-Catalyzed Cycloaddition journal April 2006
A Highly Enantioselective Hydrogenation of Silyl Enol Ethers Catalyzed by Chiral Frustrated Lewis Pairs journal August 2014
Conjugate Addition Reactions of Allylic Copper Species Derived from Grignard Reagents: Synthetic and Spectroscopic Aspects journal December 1994
Chiral Brønsted Acid as a True Catalyst: Asymmetric Mukaiyama Aldol and Hosomi–Sakurai Allylation Reactions journal May 2015
On the mechanism of the formation of alkyl-Ni(i) catalysts journal January 2021
Direct Observation of Noninnocent Reactivity of ZnBr 2 with Alkyl Halide Complexes of Nickel journal January 2004
1,5-addition of dialkylcuprate reagents to alkylcyclopropyl ketones journal January 1983
Synthesis of Quaternary Carbon Stereogenic Centers by Diastereoselective Conjugate Addition of Boron-Stabilized Allylic Nucleophiles to Enones journal May 2020
Chemistry of organosilicon compounds. 99. Conjugate addition of allylsilanes to .alpha.,.beta.-enones. A New method of stereoselective introduction of the angular allyl group in fused cyclic .alpha.,.beta.-enones journal March 1977
Visible-Light-Activated Catalytic Enantioselective β-Alkylation of α,β-Unsaturated 2-Acyl Imidazoles Using Hantzsch Esters as Radical Reservoirs journal July 2018
Preparation of new classes of aliphatic, allylic, and benzylic zinc and copper reagents by the insertion of zinc dust into organic halides, phosphates, and sulfonates journal September 1992
SmI2-Catalyzed Intermolecular Coupling of Cyclopropyl Ketones and Alkynes: A Link between Ketone Conformation and Reactivity journal February 2021
The alkylation of silyl enol ethers with SN1-unreactive iodides in the presence of silver trifluoroacetate journal March 1992
Studies on the reactions of α,β-enones with allyl indium reagent; effects of TMSCl as promoter on regioselectivity journal January 2001
Three-Component Coupling of Acyl Fluorides, Silyl Enol Ethers, and Alkynes by P(III)/P(V) Catalysis journal November 2021
Exploration of a Chiral Cobalt Catalyst for Visible‐Light‐Induced Enantioselective Radical Conjugate Addition journal August 2019
Synthesis, Electronic Structure, and Alkene Hydrosilylation Activity of Terpyridine and Bis(imino)pyridine Iron Dialkyl Complexes journal June 2012
Nickel-Catalyzed Negishi Cross-Coupling Reactions of Secondary Alkylzinc Halides and Aryl Iodides journal February 2011
Rh(III)-Catalyzed Cyclopropanation Initiated by C–H Activation: Ligand Development Enables a Diastereoselective [2 + 1] Annulation of N-Enoxyphthalimides and Alkenes journal August 2014
A Diverse Library of Chiral Cyclopropane Scaffolds via Chemoenzymatic Assembly and Diversification of Cyclopropyl Ketones journal January 2021
Stoichiometric and Catalytic Reactions of Thermally Stable Nickel(0) NHC Complexes journal January 2012
Redox-active ligands in catalysis journal January 2013
Catalytic Conjugate Addition of Allyl Groups to Styryl-Activated Enones journal February 2007
Reactions involving electron transfer. 12. Effects of solvent and substituents upon the ability of lithium diorganocuprates to add to enones journal June 1978
A stereoselective formal synthesis of (±)-(γ)-lycorane journal August 1995
Palladium-Catalyzed Saegusa–Ito Oxidation: Synthesis of α,β-Unsaturated Carbonyl Compounds from Trimethylsilyl Enol Ethers journal January 2013
A general method for the preparation of .gamma.-substituted cyclohexenals and cycloheptenals journal October 1985
One-Pot Photomediated Giese Reaction/Friedel–Crafts Hydroxyalkylation/Oxidative Aromatization To Access Naphthalene Derivatives from Toluenes and Enones journal May 2018
Asymmetric synthesis of a dopamine D1 agonist, dihydrexidine from d-serine journal July 2011
Diastereo- and Enantioselective Formal [3 + 2] Cycloaddition of Cyclopropyl Ketones and Alkenes via Ti-Catalyzed Radical Redox Relay journal February 2018
Use of Conjugated Dienones in Cyclialkylations:  Total Syntheses of Arucadiol, 1,2-Didehydromiltirone, (±)-Hinokione, (±)-Nimbidiol, Sageone, and Miltirone journal October 1997
Chiral Brønsted Acid from a Cationic Gold(I) Complex: Catalytic Enantioselective Protonation of Silyl Enol Ethers of Ketones journal August 2011
Evidence for a Ni I Active Species in the Catalytic Cross-Coupling of Alkyl Electrophiles journal July 2004
Dimethyloxosulfonium Methylide ((CH 3 ) 2 SOCH 2 ) and Dimethylsulfonium Methylide ((CH 3 ) 2 SCH 2 ). Formation and Application to Organic Synthesis journal March 1965
Stereodivergent Synthesis of Enantioenriched 4-Hydroxy-2-cyclopentenones journal December 2013
Enantioselective α-Arylation of Ketones via a Novel Cu(I)–Bis(phosphine) Dioxide Catalytic System journal February 2021
Recent Methodologies That Exploit C–C Single-Bond Cleavage of Strained Ring Systems by Transition Metal Complexes journal January 2017
A New Synthesis of Cyclopropanes1 journal August 1959
Ring opening reactions of electrophilic cyclopropanes journal July 1982
Mechanistic Studies Inform Design of Improved Ti(salen) Catalysts for Enantioselective [3 + 2] Cycloaddition journal October 2020
General approach to highly functionalized benzylic organometallics of zinc and copper journal November 1988
Regioselective allylation and alkylation of electron-deficient alkenes with organogallium and organoindium reagents journal March 1999
Conjugate addition of benzyl copper reagents to α,α-enoates and -enones. journal April 1992
Nickel-Catalyzed Regioselective Reductive Ring Opening of Aryl Cyclopropyl Ketones with Alkyl Bromides journal March 2022
Rapid Construction of a Benzo‐Fused Indoxamycin Core Enabled by Site‐Selective C−H Functionalizations journal May 2016
Stereoinvertive Nucleophilic Substitution at Quaternary Carbon Stereocenters of Cyclopropyl Ketones and Ethers journal May 2022
The chemistry of cyclopropylmethyl and related radicals journal January 1993
Effect of conformational change on reactivity in organic chemistry. Evaluations, applications, and extensions of Curtin-Hammett Winstein-Holness kinetics journal April 1983
Nickel‐Catalyzed Esterification of Aliphatic Amides journal November 2016
Selective Carbon–Carbon Bond Cleavage of Cyclopropylamine Derivatives journal June 2020
Radical Carbonyl Umpolung Arylation via Dual Nickel Catalysis journal January 2022
Investigations into the Mechanism of Inter- and Intramolecular Iron-Catalyzed [2 + 2] Cycloaddition of Alkenes journal February 2020
Organic chemistry of subvalent transition complexes. 9. Oxidative addition of nickel(0) complexes to carbon-carbon bonds in biphenylene: formation of nickelole and 1,2-dinickelecin intermediates journal February 1985
Recent Developments in Negishi Cross-Coupling Reactions journal February 2016
Visible-Light Induced Direct Synthesis of Polysubstituted Furans from Cyclopropyl Ketones journal May 2016
Si–H Bond Activation with Bullock’s Cationic Tungsten(II) Catalyst: CO as Cooperating Ligand journal November 2019

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