Enantioselective construction of C-B axially chiral alkenylborons by nickel-catalyzed radical relayed reductive coupling

Weihua Qiu, Rencai Tao, Yong He, Yao Zhou, Kai Yang () and Qiuling Song ()
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Weihua Qiu: College of Chemistry at Fuzhou University
Rencai Tao: College of Chemistry at Fuzhou University
Yong He: College of Chemistry at Fuzhou University
Yao Zhou: Hubei Normal University
Kai Yang: College of Chemistry at Fuzhou University
Qiuling Song: College of Chemistry at Fuzhou University

Nature Communications, 2024, vol. 15, issue 1, 1-9

Abstract: Abstract The catalytic asymmetric synthesis of axially chiral alkenes remains a daunting challenge due to the lower rotational barrier, especially for longer stereogenic axis (e.g. C-B axis). The asymmetric radical difunctionalization of alkynes represents an efficient strategy for these targets. Key to the success of such transformations lies in aryl-stabilized highly reactive alkenyl radical intermediates, however, it remains an elusive whether a boryl group could play a similar role. Here we report a nickel-catalyzed atroposelective radical relayed reductive coupling reaction of our designed ethynyl-azaborines with simple alkyl and aryl halides through a boron-stabilized vinyl radical intermediate. This transformation enables a straightforward access to the challenging axially chiral alkenylborons bearing a C-B axis in generally high enantioselectivity and excellent stereoselectivity.

Date: 2024
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DOI: 10.1038/s41467-024-54597-0

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