Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants

Jing Cao; Rachel Gillard; Azar Jahanbakhsh; Martin Breugst; David W. Lupton

doi:10.1021/acscatal.0c02705

Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants

Jing Cao, Rachel Gillard, Azar Jahanbakhsh, Martin Breugst, David W. Lupton

School of Chemistry

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

19 Citations (Scopus)

Abstract

An approach to the α,β-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of NHC-catalyzed reaction. In all cases, the expected products were produced with high yield and enantioselectivity, using two sets of closely related reaction conditions, without additional optimization.

Original language	English
Pages (from-to)	11791-11796
Number of pages	6
Journal	ACS Catalysis
Volume	10
Issue number	20
DOIs	https://doi.org/10.1021/acscatal.0c02705
Publication status	Published - 16 Oct 2020

Keywords

(3 + 2)-annulation
(3 + 3)-annulation
(4 + 2) annulation
enantioselective catalysis
N-heterocyclic carbene
α,β-unsaturated acyl azolium

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10.1021/acscatal.0c02705

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abstract = "An approach to the α,β-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of NHC-catalyzed reaction. In all cases, the expected products were produced with high yield and enantioselectivity, using two sets of closely related reaction conditions, without additional optimization. ",

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AU - Cao, Jing

AU - Gillard, Rachel

AU - Jahanbakhsh, Azar

AU - Breugst, Martin

AU - Lupton, David W.

PY - 2020/10/16

Y1 - 2020/10/16

N2 - An approach to the α,β-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of NHC-catalyzed reaction. In all cases, the expected products were produced with high yield and enantioselectivity, using two sets of closely related reaction conditions, without additional optimization.

AB - An approach to the α,β-unsaturated acyl azolium has been developed that exploits N-heterocyclic carbenes (NHCs) and acyl fluorides, without additional oxidants, bases, or preactivated pro-nucleophiles. These conditions have been applied in four classes of NHC-catalyzed reaction. In all cases, the expected products were produced with high yield and enantioselectivity, using two sets of closely related reaction conditions, without additional optimization.

KW - (3 + 2)-annulation

KW - (3 + 3)-annulation

KW - (4 + 2) annulation

KW - enantioselective catalysis

KW - N-heterocyclic carbene

KW - α,β-unsaturated acyl azolium

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JO - ACS Catalysis

JF - ACS Catalysis

IS - 20

ER -

Enantioselective N-Heterocyclic Carbene Catalysis via Acyl Azolium without Exogenous Oxidants

Abstract

Keywords

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