Rh(I)/NHC*-Catalyzed site- and enantioselective functionalization of c(sp3)−H bonds toward chiral triarylmethanes

Ju Hyun Kim; Steffen Greßies; Melissa Boultadakis-Arapinis; Constantin Daniliuc; Frank Glorius

doi:10.1021/acscatal.6b02392

Rh(I)/NHC*-Catalyzed site- and enantioselective functionalization of c(sp³)−H bonds toward chiral triarylmethanes

Ju Hyun Kim
, Steffen Greßies
, Melissa Boultadakis-Arapinis
, Constantin Daniliuc
, Frank Glorius

Department of Chemistry

University of Münster

Research output: Contribution to journal › Article › peer-review

101 Scopus citations

Abstract

The first Rh(I)-catalyzed asymmetric approach for the intermolecular functionalization of C(sp³)−H bonds is reported. For the first time, unsymmetrical N-heterocyclic carbenes (NHCs) were used for asymmetric catalysis that is capable of achieving not only high site-selectivity but also enantioselectivity. The Rh(I)/NHC* catalytic systems were applied to asymmetric direct C(sp³)−H arylation, which provides a synthetic route toward enantioenriched triarylmethanes.

Original language	English
Pages (from-to)	7652-7656
Number of pages	5
Journal	ACS Catalysis
Volume	6
Issue number	11
DOIs	https://doi.org/10.1021/acscatal.6b02392
State	Published - 4 Nov 2016

Keywords

Asymmetric arylation
C(sp3)−H functionalization
N-heterocyclic carbene
Triarylmethane

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10.1021/acscatal.6b02392

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title = "Rh(I)/NHC*-Catalyzed site- and enantioselective functionalization of c(sp3)−H bonds toward chiral triarylmethanes",

abstract = "The first Rh(I)-catalyzed asymmetric approach for the intermolecular functionalization of C(sp3)−H bonds is reported. For the first time, unsymmetrical N-heterocyclic carbenes (NHCs) were used for asymmetric catalysis that is capable of achieving not only high site-selectivity but also enantioselectivity. The Rh(I)/NHC* catalytic systems were applied to asymmetric direct C(sp3)−H arylation, which provides a synthetic route toward enantioenriched triarylmethanes.",

keywords = "Asymmetric arylation, C(sp3)−H functionalization, N-heterocyclic carbene, Triarylmethane",

author = "Kim, \{Ju Hyun\} and Steffen Gre{\ss}ies and Melissa Boultadakis-Arapinis and Constantin Daniliuc and Frank Glorius",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

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doi = "10.1021/acscatal.6b02392",

language = "English",

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T1 - Rh(I)/NHC*-Catalyzed site- and enantioselective functionalization of c(sp3)−H bonds toward chiral triarylmethanes

AU - Kim, Ju Hyun

AU - Greßies, Steffen

AU - Boultadakis-Arapinis, Melissa

AU - Daniliuc, Constantin

AU - Glorius, Frank

PY - 2016/11/4

Y1 - 2016/11/4

N2 - The first Rh(I)-catalyzed asymmetric approach for the intermolecular functionalization of C(sp3)−H bonds is reported. For the first time, unsymmetrical N-heterocyclic carbenes (NHCs) were used for asymmetric catalysis that is capable of achieving not only high site-selectivity but also enantioselectivity. The Rh(I)/NHC* catalytic systems were applied to asymmetric direct C(sp3)−H arylation, which provides a synthetic route toward enantioenriched triarylmethanes.

AB - The first Rh(I)-catalyzed asymmetric approach for the intermolecular functionalization of C(sp3)−H bonds is reported. For the first time, unsymmetrical N-heterocyclic carbenes (NHCs) were used for asymmetric catalysis that is capable of achieving not only high site-selectivity but also enantioselectivity. The Rh(I)/NHC* catalytic systems were applied to asymmetric direct C(sp3)−H arylation, which provides a synthetic route toward enantioenriched triarylmethanes.

KW - Asymmetric arylation

KW - C(sp3)−H functionalization

KW - N-heterocyclic carbene

KW - Triarylmethane

UR - https://www.scopus.com/pages/publications/85017512717

U2 - 10.1021/acscatal.6b02392

DO - 10.1021/acscatal.6b02392

M3 - Article

AN - SCOPUS:85017512717

SN - 2155-5435

VL - 6

SP - 7652

EP - 7656

JO - ACS Catalysis

JF - ACS Catalysis

IS - 11

ER -

Rh(I)/NHC*-Catalyzed site- and enantioselective functionalization of c(sp³)−H bonds toward chiral triarylmethanes

Abstract

Keywords

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