Metallic salt-catalyzed direct indium insertion into alkyl iodides and their applications in cross-coupling reactions

Bing Zhi Chen; Chuang Xin Wang; Zhen Hua Jing; Xue Qiang Chu; Teck Peng Loh; Zhi Liang Shen

doi:10.1039/c8qo01244j

Metallic salt-catalyzed direct indium insertion into alkyl iodides and their applications in cross-coupling reactions

Bing Zhi Chen, Chuang Xin Wang, Zhen Hua Jing, Xue Qiang Chu, Teck Peng Loh^*, Zhi Liang Shen

^*Corresponding author for this work

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

17 Citations (Scopus)

Abstract

An efficient method for the synthesis of alkyl indium reagents by means of an indium(iii) or lead(ii) halide-catalyzed direct insertion of indium into alkyl iodides and their applications in palladium-catalyzed cross-coupling reactions with aryl halides is developed. NMR and ESI-MS analyses indicated that rather than the formation of the commonly recognized alkyl indium sesquihalide with the formulation of R ₃ In ₂ X ₃ , the formed alkyl indium reagent in the present protocol should be a mixture of an alkyl indium dihalide (RInX ₂ ) and a dialkyl indium halide (R ₂ InX) (both of them presumably exist as dimers).

Original language	English
Pages (from-to)	313-318
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	6
Issue number	3
DOIs	https://doi.org/10.1039/c8qo01244j
Publication status	Published - Feb 7 2019
Externally published	Yes

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Publisher Copyright:
© 2019 the Partner Organisations.

ASJC Scopus Subject Areas

Organic Chemistry

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title = "Metallic salt-catalyzed direct indium insertion into alkyl iodides and their applications in cross-coupling reactions",

abstract = " An efficient method for the synthesis of alkyl indium reagents by means of an indium(iii) or lead(ii) halide-catalyzed direct insertion of indium into alkyl iodides and their applications in palladium-catalyzed cross-coupling reactions with aryl halides is developed. NMR and ESI-MS analyses indicated that rather than the formation of the commonly recognized alkyl indium sesquihalide with the formulation of R 3 In 2 X 3 , the formed alkyl indium reagent in the present protocol should be a mixture of an alkyl indium dihalide (RInX 2 ) and a dialkyl indium halide (R 2 InX) (both of them presumably exist as dimers).",

author = "Chen, {Bing Zhi} and Wang, {Chuang Xin} and Jing, {Zhen Hua} and Chu, {Xue Qiang} and Loh, {Teck Peng} and Shen, {Zhi Liang}",

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T1 - Metallic salt-catalyzed direct indium insertion into alkyl iodides and their applications in cross-coupling reactions

AU - Chen, Bing Zhi

AU - Wang, Chuang Xin

AU - Jing, Zhen Hua

AU - Chu, Xue Qiang

AU - Loh, Teck Peng

AU - Shen, Zhi Liang

PY - 2019/2/7

Y1 - 2019/2/7

N2 - An efficient method for the synthesis of alkyl indium reagents by means of an indium(iii) or lead(ii) halide-catalyzed direct insertion of indium into alkyl iodides and their applications in palladium-catalyzed cross-coupling reactions with aryl halides is developed. NMR and ESI-MS analyses indicated that rather than the formation of the commonly recognized alkyl indium sesquihalide with the formulation of R 3 In 2 X 3 , the formed alkyl indium reagent in the present protocol should be a mixture of an alkyl indium dihalide (RInX 2 ) and a dialkyl indium halide (R 2 InX) (both of them presumably exist as dimers).

AB - An efficient method for the synthesis of alkyl indium reagents by means of an indium(iii) or lead(ii) halide-catalyzed direct insertion of indium into alkyl iodides and their applications in palladium-catalyzed cross-coupling reactions with aryl halides is developed. NMR and ESI-MS analyses indicated that rather than the formation of the commonly recognized alkyl indium sesquihalide with the formulation of R 3 In 2 X 3 , the formed alkyl indium reagent in the present protocol should be a mixture of an alkyl indium dihalide (RInX 2 ) and a dialkyl indium halide (R 2 InX) (both of them presumably exist as dimers).

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DO - 10.1039/c8qo01244j

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Metallic salt-catalyzed direct indium insertion into alkyl iodides and their applications in cross-coupling reactions

Abstract

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