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Palladium‐Catalyzed Direct Dialkenylation of Cage BH Bonds in o ‐Carboranes through Cross‐Coupling Reactions
Author(s) -
Lyu Hairong,
Quan Yangjian,
Xie Zuowei
Publication year - 2015
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201504481
Subject(s) - regioselectivity , chemistry , palladium , reductive elimination , catalysis , alkene , decarboxylation , medicinal chemistry , coupling reaction , stereochemistry , organic chemistry
Palladium‐catalyzed direct dialkenylation of cage B(4,5)H bonds in o ‐carboranes has been achieved with the help of a carboxylic acid directing group, leading to the preparation of a series of 4,5‐[trans‐(ArCHCH)] 2 ‐ocarboranes in high yields with excellent regioselectivity. The traceless directing group, eliminated during the course of the reaction, is responsible for controlling regioselectivity and dialkenylation. A possible catalytic cycle is proposed, involving a tandem sequence of Pd II ‐initiated cage BH activation, alkene insertion, β‐H elimination, reductive elimination, and decarboxylation.