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

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

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...

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Main Authors: Chen, Xingkuan, Yang, Song, Song, Bao-An, Chi, Robin Yonggui
Other Authors: School of Physical and Mathematical Sciences
Format: Article
Language:English
Published: 2014
Subjects:
DRNTU::Science::Chemistry::Organic chemistry
Online Access:https://hdl.handle.net/10356/104209
http://hdl.handle.net/10220/19448
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Institution: Nanyang Technological University
Language: English
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spelling sg-ntu-dr.10356-1042092020-03-07T12:34:58Z Functionalization of benzylic C(sp3)H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis Chen, Xingkuan Yang, Song Song, Bao-An Chi, Robin Yonggui School of Physical and Mathematical Sciences DRNTU::Science::Chemistry::Organic chemistry 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. 2014-05-26T02:29:00Z 2019-12-06T21:28:28Z 2014-05-26T02:29:00Z 2019-12-06T21:28:28Z 2013 2013 Journal Article Chen, X., Yang, S., Song, B.-A., & Chi, Y. R. (2013). Functionalization of Benzylic C(sp3)H Bonds of Heteroaryl Aldehydes through N-Heterocyclic Carbene Organocatalysis. Angewandte Chemie International Edition, 52(42), 11134–11137. 1433-7851 https://hdl.handle.net/10356/104209 http://hdl.handle.net/10220/19448 10.1002/anie.201305861 179770 en Angewandte Chemie international edition © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
institution Nanyang Technological University
building NTU Library
country Singapore
collection DR-NTU
language English
topic DRNTU::Science::Chemistry::Organic chemistry
spellingShingle DRNTU::Science::Chemistry::Organic chemistry
Chen, Xingkuan
Yang, Song
Song, Bao-An
Chi, Robin Yonggui
Functionalization of benzylic C(sp3)H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis
description 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.
author2 School of Physical and Mathematical Sciences
author_facet School of Physical and Mathematical Sciences
Chen, Xingkuan
Yang, Song
Song, Bao-An
Chi, Robin Yonggui
format Article
author Chen, Xingkuan
Yang, Song
Song, Bao-An
Chi, Robin Yonggui
author_sort Chen, Xingkuan
title Functionalization of benzylic C(sp3)H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis
title_short Functionalization of benzylic C(sp3)H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis
title_full Functionalization of benzylic C(sp3)H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis
title_fullStr Functionalization of benzylic C(sp3)H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis
title_full_unstemmed Functionalization of benzylic C(sp3)H bonds of heteroaryl aldehydes through N-heterocyclic carbene organocatalysis
title_sort functionalization of benzylic c(sp3)h bonds of heteroaryl aldehydes through n-heterocyclic carbene organocatalysis
publishDate 2014
url https://hdl.handle.net/10356/104209
http://hdl.handle.net/10220/19448
_version_ 1681046149059837952

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