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Cobalt‐Catalyzed Regio‐ and Stereoselective Hydroboration of Allenes
Author(s) -
Li Can,
Yang Zheng,
Wang Lei,
Guo Yinlong,
Huang Zheng,
Ma Shengming
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201915716
Subject(s) - hydroboration , chemistry , allene , stereoselectivity , allylic rearrangement , cobalt , catalysis , ligand (biochemistry) , electrospray ionization , substrate (aquarium) , stereochemistry , combinatorial chemistry , medicinal chemistry , organic chemistry , ion , biochemistry , oceanography , receptor , geology
An efficient pincer‐ligand‐based cobalt‐complex‐catalyzed allene hydroboration affording Z ‐allylic boronates is described. The reaction demonstrates an excellent regio‐ as well as Z ‐stereoselectivity and a wide substrate scope that tolerates many functional groups. Based on solvent‐assisted electrospray ionization mass spectrometry (SAESI‐MS) studies, a rationale for the cobalt‐catalyzed hydroboration involving the highly selective insertion of an allene into the Co−H bond to form Z ‐allylic cobalt intermediates is proposed.