Synergistic Hydrocobaltation and Borylcobaltation Enable Regioselective Migratory Triborylation of Unactivated Alkenes
Dr. Yinsong Zhao
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543 Singapore, Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Shaozhong Ge
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543 Singapore, Singapore
Search for more papers by this authorDr. Yinsong Zhao
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543 Singapore, Singapore
Search for more papers by this authorCorresponding Author
Prof. Dr. Shaozhong Ge
Department of Chemistry, National University of Singapore, 3 Science Drive 3, 117543 Singapore, Singapore
Search for more papers by this authorAbstract
The structural diversity of sp3-triorganometallic reagents enhances their potentiality in the modular construction of molecular complexity in chemical synthesis. Despite significant achievements on the preparation of sp3 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.
Conflict of interest
The authors declare no conflict of interest.
Open Research
Data Availability Statement
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