Dehalogenative Deuteration of Unactivated Alkyl Halides Using D2O as the Deuterium Source

The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicat...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-11, Vol.84 (21), p.13841-13857
Main Authors: Xia, Aiyou, Xie, Xin, Hu, Xiaoping, Xu, Wei, Liu, Yuanhong
Format: Article
Language:English
Online Access:Get full text
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Summary:The general dehalogenation of alkyl halides with zinc using D2O or H2O as a deuterium or hydrogen donor has been developed. The method provides an efficient and economic protocol for deuterium-labeled derivatives with a wide substrate scope under mild reaction conditions. Mechanistic studies indicated that a radical process is involved for the formation of organozinc intermediates. The facile hydrolysis of the organozinc intermediates provides the driving force for this transformation.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b02026