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Title: Stable abnormal N-heterocyclic carbenes and their applications

Abstract

Although N-heterocyclic carbenes (NHCs) have been known as ligands for organometallic complexes since the 1960s, these carbenes did not attract considerable attention until Arduengo et al. reported the isolation of a metal-free imidazol-2-ylidene in 1991. In 2001 Crabtree et al. reported a few complexes featuring an NHC isomer, namely an imidazol-5-ylidene, also termed abnormal NHC (aNHCs). In 2009, it was shown that providing to protect the C-2 position of an imidazolium salt, the deprotonation occurred at the C-5 position, affording imidazol-5-ylidenes that could be isolated. Over the last ten years, stable aNHCs have been used for designing a range of catalysts employing Pd(II), Cu(I), Ni(II), Fe(0), Zn(II), Ag(I), and Au(I/III) metal based precursors. These catalysts were utilized for different organic transformations such as the Suzuki–Miyaura cross-coupling reaction, C–H bond activation, dehydrogenative coupling, Huisgen 1,3-dipolar cycloaddition (click reaction), hydroheteroarylation, hydrosilylation reaction and migratory insertion of carbenes. Main-group metal complexes were also synthesized, including K(I), Al(III), Zn(II), Sn(II), Ge(II), and Si(II/IV). Among them, K(I), Al(III), and Zn(II) complexes were used for the polymerization of caprolactone and rac-lactide at room temperature. In addition, based on the superior nucleophilicity of aNHCs, relative to that of their nNHCs isomers, they were used for small moleculesmore » activation, such as carbon dioxide (CO2), nitrous oxide (N2O), tetrahydrofuran (THF), tetrahydrothiophene and 9-borabicyclo[3.3.1]nonane (9BBN). aNHCs have also been shown to be efficient metal-free catalysts for ring opening polymerization of different cyclic esters at room temperature; they are among the most active metal-free catalysts for ε-caprolactone polymerization. Recently, aNHCs successfully accomplished the metal-free catalytic formylation of amides using CO2 and the catalytic reduction of carbon dioxide, including atmospheric CO2, into methanol, under ambient conditions. Although other transition metal complexes featuring aNHCs as ligand have been prepared and used in catalysis, this review article summarize the results obtained with the isolated aNHCs.« less

Authors:
ORCiD logo [1];  [1]; ORCiD logo [1];  [2]; ORCiD logo [2]
+ Show Author Affiliations
  1. Indian Inst. of Science Education and Research Kolkata, Mohanpur (India). Dept. of Chemical Sciences
  2. Univ. of California, San Diego, CA (United States). UCSD-CNRS Joint Research Lab. (UMI 3555). Dept. of Chemistry and Biochemistry
Publication Date:
Research Org.:
Univ. of California, San Diego, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1801904
Alternate Identifier(s):
OSTI ID: 1596170
Grant/Contract Number:  
SC0009376
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Society Reviews
Additional Journal Information:
Journal Volume: 49; Journal Issue: 4; Journal ID: ISSN 0306-0012
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Sau, Samaresh Chandra, Hota, Pradip Kumar, Mandal, Swadhin K., Soleilhavoup, Michele, and Bertrand, Guy. Stable abnormal N-heterocyclic carbenes and their applications. United States: N. p., 2020. Web. doi:10.1039/c9cs00866g.
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Sau, Samaresh Chandra, Hota, Pradip Kumar, Mandal, Swadhin K., Soleilhavoup, Michele, & Bertrand, Guy. Stable abnormal N-heterocyclic carbenes and their applications. United States. https://doi.org/10.1039/c9cs00866g
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Sau, Samaresh Chandra, Hota, Pradip Kumar, Mandal, Swadhin K., Soleilhavoup, Michele, and Bertrand, Guy. Thu . "Stable abnormal N-heterocyclic carbenes and their applications". United States. https://doi.org/10.1039/c9cs00866g. https://www.osti.gov/servlets/purl/1801904.
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@article{osti_1801904,
title = {Stable abnormal N-heterocyclic carbenes and their applications},
author = {Sau, Samaresh Chandra and Hota, Pradip Kumar and Mandal, Swadhin K. and Soleilhavoup, Michele and Bertrand, Guy},
abstractNote = {Although N-heterocyclic carbenes (NHCs) have been known as ligands for organometallic complexes since the 1960s, these carbenes did not attract considerable attention until Arduengo et al. reported the isolation of a metal-free imidazol-2-ylidene in 1991. In 2001 Crabtree et al. reported a few complexes featuring an NHC isomer, namely an imidazol-5-ylidene, also termed abnormal NHC (aNHCs). In 2009, it was shown that providing to protect the C-2 position of an imidazolium salt, the deprotonation occurred at the C-5 position, affording imidazol-5-ylidenes that could be isolated. Over the last ten years, stable aNHCs have been used for designing a range of catalysts employing Pd(II), Cu(I), Ni(II), Fe(0), Zn(II), Ag(I), and Au(I/III) metal based precursors. These catalysts were utilized for different organic transformations such as the Suzuki–Miyaura cross-coupling reaction, C–H bond activation, dehydrogenative coupling, Huisgen 1,3-dipolar cycloaddition (click reaction), hydroheteroarylation, hydrosilylation reaction and migratory insertion of carbenes. Main-group metal complexes were also synthesized, including K(I), Al(III), Zn(II), Sn(II), Ge(II), and Si(II/IV). Among them, K(I), Al(III), and Zn(II) complexes were used for the polymerization of caprolactone and rac-lactide at room temperature. In addition, based on the superior nucleophilicity of aNHCs, relative to that of their nNHCs isomers, they were used for small molecules activation, such as carbon dioxide (CO2), nitrous oxide (N2O), tetrahydrofuran (THF), tetrahydrothiophene and 9-borabicyclo[3.3.1]nonane (9BBN). aNHCs have also been shown to be efficient metal-free catalysts for ring opening polymerization of different cyclic esters at room temperature; they are among the most active metal-free catalysts for ε-caprolactone polymerization. Recently, aNHCs successfully accomplished the metal-free catalytic formylation of amides using CO2 and the catalytic reduction of carbon dioxide, including atmospheric CO2, into methanol, under ambient conditions. Although other transition metal complexes featuring aNHCs as ligand have been prepared and used in catalysis, this review article summarize the results obtained with the isolated aNHCs.},
doi = {10.1039/c9cs00866g},
journal = {Chemical Society Reviews},
number = 4,
volume = 49,
place = {United States},
year = {Thu Jan 30 00:00:00 EST 2020},
month = {Thu Jan 30 00:00:00 EST 2020}
}
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  • Bacciu, Deborha; Cavell, Kingsley J.; Fallis, Ian A.
  • Angewandte Chemie International Edition, Vol. 44, Issue 33
  • DOI: 10.1002/anie.200500884

Organocatalytic Reactions Enabled by N-Heterocyclic Carbenes
journal, May 2015

  • Flanigan, Darrin M.; Romanov-Michailidis, Fedor; White, Nicholas A.
  • Chemical Reviews, Vol. 115, Issue 17
  • DOI: 10.1021/acs.chemrev.5b00060

Stable Carbenes: From ‘Laboratory Curiosities' to Catalysis Mainstays
journal, June 2013

Recent advances in catalytic hydrogenation of carbon dioxide
journal, January 2011

  • Wang, Wei; Wang, Shengping; Ma, Xinbin
  • Chemical Society Reviews, Vol. 40, Issue 7
  • DOI: 10.1039/c1cs15008a

An Assessment of Theoretical Protocols for Calculation of the pKa Values of the Prototype Imidazolium Cation
journal, January 2004

  • Magill, Alison M.; Yates, Brian F.
  • Australian Journal of Chemistry, Vol. 57, Issue 12
  • DOI: 10.1071/CH04159

Structure and Reactivity of “Unusual” N-Heterocyclic Carbene (NHC) Palladium Complexes Synthesized from Imidazolium Salts
journal, April 2004

  • Lebel, Hélène; Janes, Marc K.; Charette, André B.
  • Journal of the American Chemical Society, Vol. 126, Issue 16
  • DOI: 10.1021/ja049759r

1 H -1,2,3-Triazol-5-ylidenes: Readily Available Mesoionic Carbenes
journal, November 2018

  • Guisado-Barrios, Gregorio; Soleilhavoup, Michèle; Bertrand, Guy
  • Accounts of Chemical Research, Vol. 51, Issue 12
  • DOI: 10.1021/acs.accounts.8b00480

Direct Synthesis of a Mercury Salt-Carbene Complex
journal, February 1968

  • Wanzlick, H. -W.; Schönherr, H. -J.
  • Angewandte Chemie International Edition in English, Vol. 7, Issue 2
  • DOI: 10.1002/anie.196801412

Introduction: Carbene Chemistry
journal, March 2018

Constructing a Stable Carbene with a Novel Topology and Electronic Framework
journal, November 2003

  • Bazinet, Patrick; Yap, Glenn P. A.; Richeson, Darrin S.
  • Journal of the American Chemical Society, Vol. 125, Issue 44
  • DOI: 10.1021/ja0372661

Stability and Electronic Properties of Imidazole-Based Mesoionic Carbenes
journal, June 2011

[Bis(diisopropylamino)phosphino]trimethylsilylcarbene: A Stable Nucleophilic Carbene
journal, May 1989

  • Igau, Alai; Baceiredo, Antoine; Trinquier, Georges
  • Angewandte Chemie International Edition in English, Vol. 28, Issue 5
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Reduction of CO 2 to Trimethoxyboroxine with BH 3 in THF
journal, October 2014

  • Fujiwara, Koji; Yasuda, Shogo; Mizuta, Tsutomu
  • Organometallics, Vol. 33, Issue 22
  • DOI: 10.1021/om5008488

A Bis-Carbenealkenyl Copper(I) Complex from a Tripodal Tris-Carbene Ligand
journal, July 2003

  • Hu, Xile; Castro-Rodriguez, Ingrid; Meyer, Karsten
  • Organometallics, Vol. 22, Issue 15
  • DOI: 10.1021/om0304006

N-Heterocyclic Pincer Dicarbene Complexes of Iron(II):  C-2 and C-5 Metalated Carbenes on the Same Metal Center
journal, January 2004

  • Danopoulos, Andreas A.; Tsoureas, Nikolaos; Wright, Joseph A.
  • Organometallics, Vol. 23, Issue 2
  • DOI: 10.1021/om0341911

Copper(I) 1,2,3-Triazol-5-ylidene Complexes as Efficient Catalysts for Click Reactions of Azides with Alkynes
journal, February 2011

  • Nakamura, Tatsuhito; Terashima, Takahiro; Ogata, Kenichi
  • Organic Letters, Vol. 13, Issue 4
  • DOI: 10.1021/ol102858u

Electronic stabilization of nucleophilic carbenes
journal, July 1992

  • Arduengo, Anthony J.; Dias, H. V. Rasika; Harlow, Richard L.
  • Journal of the American Chemical Society, Vol. 114, Issue 14
  • DOI: 10.1021/ja00040a007

Efficient catalytic addition of aromatic carbon-hydrogen bonds to olefins
journal, December 1993

  • Murai, Shinji; Kakiuchi, Fumitoshi; Sekine, Shinya
  • Nature, Vol. 366, Issue 6455
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Copper(I) Complexes Bearing Carbenes Beyond Classical N-Heterocyclic Carbenes: Synthesis and Catalytic Activity in “Click Chemistry”
journal, October 2015

  • Bidal, Yannick D.; Lesieur, Mathieu; Melaimi, Mohand
  • Advanced Synthesis & Catalysis, Vol. 357, Issue 14-15
  • DOI: 10.1002/adsc.201500453

CO 2 Capture from Ambient Air by Crystallization with a Guanidine Sorbent
journal, December 2016

  • Seipp, Charles A.; Williams, Neil J.; Kidder, Michelle K.
  • Angewandte Chemie International Edition, Vol. 56, Issue 4
  • DOI: 10.1002/anie.201610916

1,3-Dimethyl-4-imidazolinyliden-(2)-pentacarbonylchrom ein neuer übergangsmetall-carben-komplex
journal, June 1968

Nickel-Catalyzed C(sp 2 )–H Borylation of Arenes
journal, August 2019

One-Pot Consecutive Catalysis by Integrating Organometallic Catalysis with Organocatalysis
journal, August 2014

  • Sau, Samaresh Chandra; Roy, Sudipta Raha; Mandal, Swadhin K.
  • Chemistry - An Asian Journal, Vol. 9, Issue 10
  • DOI: 10.1002/asia.201402363

Beyond Conventional N -Heterocyclic Carbenes: Abnormal, Remote, and Other Classes of NHC Ligands with Reduced Heteroatom Stabilization
journal, August 2009

  • Schuster, Oliver; Yang, Liangru; Raubenheimer, Helgard G.
  • Chemical Reviews, Vol. 109, Issue 8
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Atroposelective Total Synthesis of Axially Chiral Biaryl Natural Products
journal, February 2011

  • Bringmann, Gerhard; Gulder, Tanja; Gulder, Tobias A. M.
  • Chemical Reviews, Vol. 111, Issue 2
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Water splitting–biosynthetic system with CO 2 reduction efficiencies exceeding photosynthesis
journal, June 2016

Abnormal N-heterocyclic carbene main group organometallic chemistry: a debut to the homogeneous catalysis
journal, January 2013

  • Sen, Tamal K.; Sau, Samaresh Chandra; Mukherjee, Arup
  • Dalton Transactions, Vol. 42, Issue 39
  • DOI: 10.1039/c3dt51802g

Sulfonamide, Phenolate, and Directing Ligand-Free Indium Initiators for the Ring-Opening Polymerization of rac -Lactide
journal, March 2011

  • Blake, Matthew P.; Schwarz, Andrew D.; Mountford, Philip
  • Organometallics, Vol. 30, Issue 5
  • DOI: 10.1021/om101166s

An abnormal N-heterocyclic carbene based nickel complex for catalytic reduction of nitroarenes
journal, January 2016

  • Vijaykumar, Gonela; Mandal, Swadhin K.
  • Dalton Transactions, Vol. 45, Issue 17
  • DOI: 10.1039/C6DT00470A

Stable Cyclic Carbenes and Related Species beyond Diaminocarbenes
journal, September 2010

  • Melaimi, Mohand; Soleilhavoup, Michèle; Bertrand, Guy
  • Angewandte Chemie International Edition, Vol. 49, Issue 47
  • DOI: 10.1002/anie.201000165

Peptidotriazoles on Solid Phase  [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides
journal, May 2002

  • Tornøe, Christian W.; Christensen, Caspar; Meldal, Morten
  • The Journal of Organic Chemistry, Vol. 67, Issue 9, p. 3057-3064
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Bonding Analysis of N-Heterocyclic Carbene Tautomers and Phosphine Ligands in Transition-Metal Complexes: A Theoretical Study
journal, December 2007

  • Tonner, Ralf; Heydenrych, Greta; Frenking, Gernot
  • Chemistry – An Asian Journal, Vol. 2, Issue 12
  • DOI: 10.1002/asia.200700235

Abnormally Bound N-Heterocyclic Carbene Complexes of Ruthenium: CH Activation of Both C4 and C5 Positions in the Same Ligand
journal, August 2007

  • Ellul, Charles E.; Mahon, Mary F.; Saker, Olly
  • Angewandte Chemie, Vol. 119, Issue 33
  • DOI: 10.1002/ange.200701930

Selective Reduction of Esters to Aldehydes under the Catalysis of Well-Defined NHC-Iron Complexes
journal, June 2013

  • Li, Haoquan; Misal Castro, Luis C.; Zheng, Jianxia
  • Angewandte Chemie, Vol. 125, Issue 31
  • DOI: 10.1002/ange.201303003

1,3-Dialkyl- and 1,3-Diaryl-3,4,5,6-tetrahydropyrimidin-2-ylidene Rhodium(i) and Palladium(II) Complexes: Synthesis, Structure, and Reactivity
journal, June 2004

  • Mayr, Monika; Wurst, Klaus; Ongania, Karl-Hans
  • Chemistry - A European Journal, Vol. 10, Issue 11
  • DOI: 10.1002/chem.200490038

Beyond Oil and Gas: The Methanol Economy
journal, July 2005

Analysis of the Reactions Used for the Preparation of Drug Candidate Molecules
journal, October 2006

F-Block N-Heterocyclic Carbene Complexes
journal, January 2007

Transformation of Carbon Dioxide
journal, September 2007

  • Sakakura, Toshiyasu; Choi, Jun-Chul; Yasuda, Hiroyuki
  • ChemInform, Vol. 38, Issue 36
  • DOI: 10.1002/chin.200736261

Platinum-Mediated Oxidative Addition and Reductive Elimination of Imidazolium Salts at C4 and C5
journal, August 2005

  • Bacciu, Deborha; Cavell, Kingsley J.; Fallis, Ian A.
  • Angewandte Chemie, Vol. 117, Issue 33
  • DOI: 10.1002/ange.200500884

Neutral Ligands with Exceptional Donor Ability for Palladium-Catalyzed Alkene Hydrogenation
journal, August 2007

  • Heckenroth, Marion; Kluser, Evelyne; Neels, Antonia
  • Angewandte Chemie, Vol. 119, Issue 33
  • DOI: 10.1002/ange.200702199

N-Heterocyclic Carbenes as Organocatalysts
journal, July 2007

  • Marion, Nicolas; Diez-Gonzales, Silvia; Nolan, Steven P.
  • ChemInform, Vol. 38, Issue 28
  • DOI: 10.1002/chin.200728246

N-Heterocyclic Carbenes
journal, January 2011

  • Arduengo, Anthony J.
  • Australian Journal of Chemistry, Vol. 64, Issue 8
  • DOI: 10.1071/ch11249

A Diagonal Approach to Chemical Recycling of Carbon Dioxide: Organocatalytic Transformation for the Reductive Functionalization of CO2
journal, September 2011

  • Das Neves Gomes, Christophe; Jacquet, Olivier; Villiers, Claude
  • Angewandte Chemie, Vol. 124, Issue 1
  • DOI: 10.1002/ange.201105516

Hydrogenations at Room Temperature and Atmospheric Pressure with Mesoionic Carbene-Stabilized Borenium Catalysts
journal, January 2015

  • Eisenberger, Patrick; Bestvater, Brian P.; Keske, Eric C.
  • Angewandte Chemie, Vol. 127, Issue 8
  • DOI: 10.1002/ange.201409250

Controlled Ring-Opening Polymerization of Lactide and Glycolide
journal, April 2005

  • Dechy-Cabaret, Odile; Martin-Vaca, Blanca; Bourissou, Didier
  • ChemInform, Vol. 36, Issue 14
  • DOI: 10.1002/chin.200514262

Imidazo[1,5-a]pyridine: A Versatile Architecture for Stable N-Heterocyclic Carbenes.
journal, August 2005

  • Alcarazo, Manuel; Roseblade, Stephen J.; Cowley, Andrew R.
  • ChemInform, Vol. 36, Issue 31
  • DOI: 10.1002/chin.200531146

Mesoionic and Related Less Heteroatom-Stabilized N-Heterocyclic Carbene Complexes: Synthesis, Catalysis, and Other Applications
text, January 2018

  • Vivancos Ureña, Angela; Segarra Almela, Maria De La Candelaria; Albrecht, Martin
  • American Chemical Society
  • DOI: 10.7892/boris.120428
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