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Aryl Chloride-Directed Enantioselective C(sp2)‑H Borylation Enabled by Iridium Catalysis

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journal contribution
posted on 2023-11-07, 20:42 authored by Hongliang Zhao, Chao-Yue Zhao, Lili Chen, Chungu Xia, Xin Hong, Senmiao Xu
We herein report the iridium-catalyzed enantioselective C–H borylation of aryl chlorides. A variety of prochiral biaryl compounds could be well-tolerated, affording a vast array of axially chiral biaryls with high enantioselectivities. The current method exhibits a high turnover number (TON) of 7000, which represents the highest in functional-group-directed asymmetric C–H activation. The high TON was attributed to a weak catalyst-substrate interaction that was caused by mismatched chirality between catalyst and substrate. We also demonstrated the synthetic application of the current method by C–B, ortho-C–H, and C–Cl bond functionalization, including programmed Suzuki–Miyaura coupling for the synthesis of axially chiral polyarenes.

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