Palladium-Catalyzed Cross-Coupling of gem-Bis(boronates) with Aryl Halides: An Alternative To Access Quaternary α-Aryl Aldehydes

Purui Zheng, Yujie Zhai, Xiaoming Zhao*, Tao XU*

*School of Chemical Science and Engineering, Tongji University, 1239 Siping Road, Shanghai, 200092, P. R. of China, Email: xmzhao08mail.tongji.edu.cn, taoxumail.tongji.edu.cn

P. Zheng, Y. Zhai, X. Zhao, T. Xu, Org. Lett., 2019, 21, 393-396.

DOI: 10.1021/acs.orglett.8b03560

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Abstract

The use of gem-bis(boronates) as precursors enables a construction of quaternary α-aryl aldehydes, in which both groups are installed simultaneously. This methodology provides a general strategy to produce quaternary α-aryl aldehydes with broad scopes and synthetic convenience. In addition, gem-bis(boronates) are readily available from ketones.

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proposed mechanism

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Key Words

carbonyl compounds, arylation, alkenylation

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ID: J54-Y2019