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Haloboration of Internal Alkynes with Boronium and Borenium Cations as a Route to Tetrasubstituted Alkenes
Author(s) -
Lawson James R.,
Clark Ewan R.,
Cade Ian A.,
Solomon Sophia A.,
Ingleson Michael J.
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201302609
Subject(s) - chemistry
Hail boration! 2‐Dimethylaminopyridine‐ligated dihaloborocations [X 2 B(2‐DMAP)] + with a strained four‐membered boracycle were used for the haloboration of terminal and dialkyl internal alkynes (see scheme). Esterification then provided vinyl boronate esters as useful precursors to tetrasubstituted alkenes. Following mechanistic studies, the scope of the haloboration was expanded simply by variation of the amine. Pin=2,3‐dimethyl‐2,3‐butanedioxy.