Selective Activation of Unstrained C(O)–C Bond in Ketone Suzuki–Miyaura Coupling Reaction Enabled by Hydride-Transfer Strategy

A Rh­(I)-catalyzed ketone Suzuki–Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C­(O)–C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-positio...

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Bibliographic Details
Published in:Organic letters 2022-02, Vol.24 (6), p.1372-1377
Main Authors: Zhong, Jing, Zhou, Wuxin, Yan, Xufei, Xia, Ying, Xiang, Haifeng, Zhou, Xiangge
Format: Article
Language:English
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Summary:A Rh­(I)-catalyzed ketone Suzuki–Miyaura coupling reaction of benzylacetone with arylboronic acid is developed. Selective C­(O)–C bond activation, which employs aminopyridine as a temporary directing group and ethyl vinyl ketone as a hydride acceptor, occurs on the alkyl chain containing a β-position hydrogen. A series of acetophenone products were obtained in yields up to 75%.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c00110