Functionalization of benzylic C(sp3)-H bonds of heteroaryl aldehydes through N-Heterocyclic carbene organocatalysis

Xingkuan Chen; Song Yang; Bao An Song; Yonggui Robin Chi

doi:10.1002/anie.201305861

Functionalization of benzylic C(sp³)-H bonds of heteroaryl aldehydes through N-Heterocyclic carbene organocatalysis

Xingkuan Chen, Song Yang, Bao An Song, Yonggui Robin Chi

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

162 Citations (Scopus)

Abstract

Aryl aldehyde activation: Oxidative activation of 2-methylindole-3- carboxaldehyde (I) through N-heterocyclic carbene (NHC) organocatalysis generates heterocyclic ortho-quinodimethane (II) as a key intermediate. This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones or isatins to form polycyclic lactones containing a quaternary carbon center.

Original language	English
Pages (from-to)	11134-11137
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	52
Issue number	42
DOIs	https://doi.org/10.1002/anie.201305861
Publication status	Published - Oct 11 2013
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

C-H functionalization
indoles
N-heterocyclic carbenes
spiro compounds
synthetic methods

Access to Document

10.1002/anie.201305861

Cite this

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abstract = "Aryl aldehyde activation: Oxidative activation of 2-methylindole-3- carboxaldehyde (I) through N-heterocyclic carbene (NHC) organocatalysis generates heterocyclic ortho-quinodimethane (II) as a key intermediate. This intermediate then undergoes formal [4+2] cycloaddition with trifluoromethyl ketones or isatins to form polycyclic lactones containing a quaternary carbon center.",

keywords = "C-H functionalization, indoles, N-heterocyclic carbenes, spiro compounds, synthetic methods",

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AU - Song, Bao An

AU - Chi, Yonggui Robin

PY - 2013/10/11

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KW - N-heterocyclic carbenes

KW - spiro compounds

KW - synthetic methods

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