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Rhodium‐Catalyzed P III ‐Directed ortho ‐C−H Borylation of Arylphosphines
Author(s) -
Wen Jian,
Wang Dingyi,
Qian Jiasheng,
Wang Di,
Zhu Chendan,
Zhao Yue,
Shi Zhuangzhi
Publication year - 2019
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201813452
Subject(s) - borylation , rhodium , metalation , chemistry , catalysis , phosphine , chelation , ring (chemistry) , medicinal chemistry , transition metal , stereochemistry , iridium , organic chemistry , aryl , alkyl
Transition‐metal‐mediated metalation of an aromatic C−H bond that is adjacent to a tertiary phosphine group in arylphosphines via a four‐membered chelate ring was first discovered in 1968. Herein, we overcome a long‐standing problem with the ortho ‐C−H activation of arylphosphines in a catalytic fashion. In particular, we developed a rhodium‐catalyzed ortho ‐selective C−H borylation of various commercially available arylphosphines with B 2 pin 2 through P III ‐chelation‐assisted C−H activation. This discovery is suggestive of a generic platform that could enable the late‐stage modification of readily accessible arylphosphines.