Inexpensive Radical Methylation and Related Alkylations of Heteroarenes

Qi Huang; Samir Z. Zard

doi:10.1021/acs.orglett.8b00190

Inexpensive Radical Methylation and Related Alkylations of Heteroarenes

Qi Huang
, Samir Z. Zard

Laboratoire de Synthèse Organique

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

Abstract

A simple method for the introduction of a methyl and higher aliphatic group to various heteroarenes using very inexpensive reagents is described. It is based on the radical addition of a carboxylic xanthate followed by decarboxylation. Depending on the heteroarene structure, the decarboxylation can be spontaneous or induced by heating in N,N-dimethylacetamide or N-methyl pyrrolidone in a microwave oven.

Original language	English
Pages (from-to)	1413-1416
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	5
DOIs	https://doi.org/10.1021/acs.orglett.8b00190
Publication status	Published - 2 Mar 2018
Externally published	Yes

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title = "Inexpensive Radical Methylation and Related Alkylations of Heteroarenes",

abstract = "A simple method for the introduction of a methyl and higher aliphatic group to various heteroarenes using very inexpensive reagents is described. It is based on the radical addition of a carboxylic xanthate followed by decarboxylation. Depending on the heteroarene structure, the decarboxylation can be spontaneous or induced by heating in N,N-dimethylacetamide or N-methyl pyrrolidone in a microwave oven.",

author = "Qi Huang and Zard, \{Samir Z.\}",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

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doi = "10.1021/acs.orglett.8b00190",

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AB - A simple method for the introduction of a methyl and higher aliphatic group to various heteroarenes using very inexpensive reagents is described. It is based on the radical addition of a carboxylic xanthate followed by decarboxylation. Depending on the heteroarene structure, the decarboxylation can be spontaneous or induced by heating in N,N-dimethylacetamide or N-methyl pyrrolidone in a microwave oven.

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DO - 10.1021/acs.orglett.8b00190

M3 - Article

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JO - Organic Letters

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Inexpensive Radical Methylation and Related Alkylations of Heteroarenes

Abstract

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