Indium-copper and indium-silver mediated Barbier-Grignard-type alkylation reaction of aldehydes using unactivated alkyl halides in water

Zhi Liang Shen; Yan Lin Yeo; Teck Peng Loh

doi:10.1021/jo8000589

Indium-copper and indium-silver mediated Barbier-Grignard-type alkylation reaction of aldehydes using unactivated alkyl halides in water

Zhi Liang Shen, Yan Lin Yeo, Teck Peng Loh^*

^*Corresponding author for this work

Nanyang Technological University

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

56 Citations (Scopus)

Abstract

(Chemical Equation Presented) An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I₂ or In/AgI/I₂ system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I ₂ were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.

Original language	English
Pages (from-to)	3922-3924
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	73
Issue number	10
DOIs	https://doi.org/10.1021/jo8000589
Publication status	Published - May 16 2008
Externally published	Yes

ASJC Scopus Subject Areas

Organic Chemistry

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abstract = "(Chemical Equation Presented) An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I2 or In/AgI/I2 system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I 2 were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.",

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AU - Yeo, Yan Lin

AU - Loh, Teck Peng

PY - 2008/5/16

Y1 - 2008/5/16

N2 - (Chemical Equation Presented) An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I2 or In/AgI/I2 system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I 2 were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.

AB - (Chemical Equation Presented) An efficient method has been developed for the Barbier-Grignard-type alkylation reaction of aldehydes (including aliphatic version) using unactivated alkyl halides in water in the presence of an In/CuI/I2 or In/AgI/I2 system. The reactions proceeded more efficiently in water than in organic solvent. In, CuI or AgI, and I 2 were all essential for the efficient progress of the reactions. A radical-type reaction mechanism was studied and proposed by using 4-pentenal as substrate.

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Indium-copper and indium-silver mediated Barbier-Grignard-type alkylation reaction of aldehydes using unactivated alkyl halides in water

Abstract

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