Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 61, Issue 14, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202116133
Keywords
Allylic Boronates; Borylation; Cobalt; Synergistic Catalysis; Unactivated Alkenes
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Funding
- Ministry of Education (MOE) of Singapore [R-143-000-A93-112]
- A*STAR under its AME IRG Grant [A20E5c0097]
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The structural diversity of sp(3)-triorganometallic reagents enhances their potential in modular construction of molecular complexity in chemical synthesis. We report a selective triborylation reaction of unactivated alkenes to access synthetically versatile 1,1,3-triborylalkanes. This reaction provides a general platform for regioselective trifunctionalization of unactivated alkenes, and its utility is highlighted by the synthesis of various value-added chemicals from readily accessible unactivated alkenes.
The structural diversity of sp(3)-triorganometallic reagents enhances their potentiality in the modular construction of molecular complexity in chemical synthesis. Despite significant achievements on the preparation of sp(3) 1,1,1- and 1,1,2-triorganometallic B,B,B-reagents, catalytic approaches that enable the installation of multiple boryl groups at skipped carbons of unactivated alkenes still remain elusive. Herein, we report a cobalt-catalyzed selective triborylation reaction of unactivated alkenes to access synthetically versatile 1,1,3-triborylalkanes. This triborylation protocol provides a general platform for regioselective trifunctionalization of unactivated alkenes, and its utility is highlighted by the synthesis of various value-added chemicals from readily accessible unactivated alkenes. Mechanistic studies, including deuterium-labelling experiments and evaluation of potential reactive intermediates, provide insight into the experimentally observed chemo- and regioselectivity.
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