Direct synthesis of water-tolerant alkyl indium reagents and their application in palladium-catalyzed couplings with aryl halides

Zhi Liang Shen; Kelvin Kau Kiat Goh; Yong Sheng Yang; Yin Chang Lai; Colin Hong An Wong; Hao Lun Cheong; Teck Peng Loh

doi:10.1002/anie.201005798

Direct synthesis of water-tolerant alkyl indium reagents and their application in palladium-catalyzed couplings with aryl halides

Zhi Liang Shen, Kelvin Kau Kiat Goh, Yong Sheng Yang, Yin Chang Lai, Colin Hong An Wong, Hao Lun Cheong, Teck Peng Loh^*

^*Corresponding author for this work

Nanyang Technological University

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

49 Citations (Scopus)

Abstract

A direct result: Alkyl indium reagents are synthesized by the insertion of indium into alkyl halide mediated by CuCl. The synthetic utility of these reagents is demonstrated by their palladium-catalyzed coupling with aryl halides (see scheme). The reagents are compatible with various functional groups, and this makes the protocol generally useful in organic synthesis. DMA=N,N-dimethylacetamide, TBS=tert-butyldimethylsilyl.

Original language	English
Pages (from-to)	511-514
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	50
Issue number	2
DOIs	https://doi.org/10.1002/anie.201005798
Publication status	Published - Jan 10 2011
Externally published	Yes

ASJC Scopus Subject Areas

Catalysis
General Chemistry

Keywords

cross - coupling
indium
organoindium reagents
palladium
synthesis design

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10.1002/anie.201005798

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abstract = "A direct result: Alkyl indium reagents are synthesized by the insertion of indium into alkyl halide mediated by CuCl. The synthetic utility of these reagents is demonstrated by their palladium-catalyzed coupling with aryl halides (see scheme). The reagents are compatible with various functional groups, and this makes the protocol generally useful in organic synthesis. DMA=N,N-dimethylacetamide, TBS=tert-butyldimethylsilyl.",

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T1 - Direct synthesis of water-tolerant alkyl indium reagents and their application in palladium-catalyzed couplings with aryl halides

AU - Shen, Zhi Liang

AU - Goh, Kelvin Kau Kiat

AU - Yang, Yong Sheng

AU - Lai, Yin Chang

AU - Wong, Colin Hong An

AU - Cheong, Hao Lun

AU - Loh, Teck Peng

PY - 2011/1/10

Y1 - 2011/1/10

N2 - A direct result: Alkyl indium reagents are synthesized by the insertion of indium into alkyl halide mediated by CuCl. The synthetic utility of these reagents is demonstrated by their palladium-catalyzed coupling with aryl halides (see scheme). The reagents are compatible with various functional groups, and this makes the protocol generally useful in organic synthesis. DMA=N,N-dimethylacetamide, TBS=tert-butyldimethylsilyl.

AB - A direct result: Alkyl indium reagents are synthesized by the insertion of indium into alkyl halide mediated by CuCl. The synthetic utility of these reagents is demonstrated by their palladium-catalyzed coupling with aryl halides (see scheme). The reagents are compatible with various functional groups, and this makes the protocol generally useful in organic synthesis. DMA=N,N-dimethylacetamide, TBS=tert-butyldimethylsilyl.

KW - cross - coupling

KW - indium

KW - organoindium reagents

KW - palladium

KW - synthesis design

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Direct synthesis of water-tolerant alkyl indium reagents and their application in palladium-catalyzed couplings with aryl halides

Abstract

ASJC Scopus Subject Areas

Keywords

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