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Zwitterion‐Initiated Hydroboration of Alkynes and Styrene
Author(s) -
Bismuto Alessandro,
Cowley Michael J.,
Thomas Stephen P.
Publication year - 2021
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.202001323
Subject(s) - hydroboration , chemistry , borane , zwitterion , styrene , alkyne , catalysis , medicinal chemistry , organic chemistry , copolymer , molecule , polymer
Abstract The hydroboration of alkynes and styrene with HBpin has been developed using tris(pentaflurophenyl)borane (B(C 6 F 5 ) 3 ) as the initiator of catalysis. The hydroboration is proposed to be initiated by Lewis acid activation of the alkyne by (B(C 6 F 5 ) 3 ) to form a highly reactive zwitterionic species which subsequently react with HBpin to give the alkenyl boronic ester. This zwitterion has also showed potential to be a competent catalyst for the hydroboration of styrene. The zwitterionic intermediate is analogous to that proposed in the Piers borane‐catalysed hydroboration and 1,1‐carboboration of alkynes with B(C 6 F 5 ) 3.