Synthesis of P-chiral phosphine compounds by palladium-catalyzed C–P coupling reactions

Cuiying Wang; Chang-Duo Yue; Jia Yuan; Jia-Lian Zheng; Ying Zhang; Hong Yu; Jian Chen; Sixuan Meng; Yang Yu; Guang-Ao Yu; Chi-Ming Che

doi:10.1039/D0CC05340F

Synthesis of P-chiral phosphine compounds by palladium-catalyzed C–P coupling reactions†

Cuiying Wang,‡^a Chang-Duo Yue,‡^a Jia Yuan,*^a Jia-Lian Zheng,^a Ying Zhang,^a Hong Yu,^a Jian Chen,^a Sixuan Meng,^a Yang Yu,^b Guang-Ao Yu

*^a and Chi-Ming Che

*^c

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* Corresponding authors

^a Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, and Chemical Biology Center, College of Chemistry, Central China Normal University, Wuhan 430079, China
E-mail: yuguang@mail.ccnu.edu.cn

^b Department of Chemistry, Southern University of Science and Technology, Shenzhen 518055, China

^c State Key Laboratory of Synthetic Chemistry and Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, China
E-mail: cmche@hku.hk

Abstract

An efficient C–P coupling reaction of enantiopure tert-butylmethylphosphine-boranes with aryl and heteroaryl halides is developed by using Pd(OAc)₂/dppf as a catalyst, affording a series of (S) or (R)-P-chiral phosphines in moderate to high yields and with ee values up to 99% ee. Moreover, the reaction time could be reduced from 72 h to 6 h with increased ee values under microwave irradiation.

Chemical Communications

Synthesis of P-chiral phosphine compounds by palladium-catalyzed C–P coupling reactions†

Abstract

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Synthesis of P-chiral phosphine compounds by palladium-catalyzed C–P coupling reactions

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