C-C and C-X coupling reactions of unactivated alkyl electrophiles using copper catalysis

Transition metal-catalysed cross-coupling reactions are widely used for construction of carbon-carbon and carbon-heteroatom bonds. However, compared to aryl or alkenyl electrophiles, the cross-coupling of unactivated alkyl electrophiles containing β hydrogens remains a challenge. Over the past few y...

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Published inChemical Society reviews Vol. 49; no. 22; pp. 836 - 864
Main Authors Cheng, Li-Jie, Mankad, Neal P
Format Journal Article
LanguageEnglish
Published England Royal Society of Chemistry 21.11.2020
Subjects
Aromatic compounds
Carbenes
Carbon
Chemical reactions
Copper
Cross coupling
Phosphines
Reagents
Transition metals
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Summary:Transition metal-catalysed cross-coupling reactions are widely used for construction of carbon-carbon and carbon-heteroatom bonds. However, compared to aryl or alkenyl electrophiles, the cross-coupling of unactivated alkyl electrophiles containing β hydrogens remains a challenge. Over the past few years, the use of suitable ligands such as bulky phosphines or N-heterocyclic carbenes (NHCs) has enabled reactions of unactivated alkyl electrophiles not only limited to the traditional cross-coupling with Grignard reagents, but also including a diverse range of organic transformations via either S N 2 or radical pathways. This review provides a comprehensive overview of the recent development in copper-catalysed C-C, C-N, C-B, C-Si and C-F bond-forming reactions using unactivated alkyl electrophiles. Copper catalysts enable cross-coupling reactions of unactivated alkyl electrophiles to generate C-C and C-X bonds.
Bibliography:Li-Jie Cheng obtained his BS degree in 2008 from Hebei University in China and PhD degree in 2013 from Nankai University under the supervision of Professor Qi-Lin Zhou. Then he moved to Imperial College London, working as a research associate with Professor Chris Cordier from 2013-2016. Since August 2016, he joined Professor Neal Mankad's group to continue his postdoctoral studies at University of Illinois at Chicago. His research in the Mankad group has focused on transition metal-catalyzed carbonylative coupling reactions as well as heterobimetallic catalysis.
Neal Mankad has been studying Cu catalysts since 2001, when he first began conducting undergraduate research under the supervision of Joseph Sadighi at MIT. After doing PhD research as an NSF Graduate Research Fellow at Caltech with Jonas Peters and postdoctoral research as a NIH NRSA Postdoctoral Fellow at University of California-Berkeley with Dean Toste, he began his independent career at University of Illinois at Chicago in 2012, earning a Sloan Fellowship in 2015 and promotion with tenure in 2018. The Mankad Group studies Cu-catalyzed radical carbonylation reactions, heterobinuclear catalysts containing Cu, and metalloenzyme active sites featuring Cu clusters.
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ISSN:0306-0012
1460-4744
DOI:10.1039/d0cs00316f