Rhodium-catalyzed selective direct arylation of phosphines with aryl bromides

Dingyi Wang, Mingjie Li, Chengdong Shuang (), Yong Liang, Yue Zhao, Minyan Wang () and Zhuangzhi Shi ()
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Dingyi Wang: Nanjing University
Mingjie Li: Nanjing University
Chengdong Shuang: Nanjing University
Yong Liang: Nanjing University
Yue Zhao: Nanjing University
Minyan Wang: Nanjing University
Zhuangzhi Shi: Nanjing University

Nature Communications, 2022, vol. 13, issue 1, 1-10

Abstract: Abstract The widespread use of phosphine ligand libraries is frequently hampered by the challenges associated with their modular preparation. Here, we report a protocol that appends arenes to arylphosphines to access a series of biaryl monophosphines via rhodium-catalyzed P(III)-directed ortho C–H activation, enabling unprecedented one-fold, two-fold, and three-fold direct arylation. Our experimental and theoretical findings reveal a mechanism involving oxidative addition of aryl bromides to the Rh catalyst, further ortho C–H metalation via a four-membered cyclometalated ring. Given the ready availability of substrates, our approach opens the door to developing more general methods for the construction of phosphine ligands.

Date: 2022
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DOI: 10.1038/s41467-022-30697-7

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