Atroposelective hydroarylation of biaryl phosphines directed by phosphorus centres

Zexian Li, Minyan Wang, Youqing Yang, Yong Liang, Xiangyang Chen, Yue Zhao, K. N. Houk and Zhuangzhi Shi ()
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Zexian Li: Huaibei Normal University
Minyan Wang: Nanjing University
Youqing Yang: Huaibei Normal University
Yong Liang: Nanjing University
Xiangyang Chen: University of California
Yue Zhao: Nanjing University
K. N. Houk: University of California
Zhuangzhi Shi: Huaibei Normal University

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract Prized for their ability to generate chemical complexity rapidly, catalytic carbon–hydrogen (C–H) activation and functionalization reactions have enabled a paradigm shift in the standard logic of synthetic chemistry. Directing group strategies have been used extensively in C–H activation reactions to control regio- and enantioselectivity with transition metal catalysts. However, current methods rely heavily on coordination with nitrogen and/or oxygen atoms in molecules and have therefore been found to exhibit limited generality in asymmetric syntheses. Here, we report enantioselective C–H activation with unsaturated hydrocarbons directed by phosphorus centres to rapidly construct libraries of axially chiral phosphines through dynamic kinetic resolution. High reactivity and enantioselectivity are derived from modular assembly of an iridium catalyst with an endogenous phosphorus atom and an exogenous chiral phosphorus ligand, as confirmed by detailed experimental and computational studies. This reaction mode significantly expands the pool of enantiomerically enriched functional phosphines, some of which have shown excellent efficiency for asymmetric catalysis.

Date: 2023
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DOI: 10.1038/s41467-023-44202-1

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