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Facial Synthesis of o ‐Carborane‐Substituted Alkenes and Allenes by a Regioselective Ene Reaction of 1,3‐Dehydro‐ o ‐carborane
Author(s) -
Zhao Da,
Zhang Jiji,
Xie Zuowei
Publication year - 2015
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201501911
Subject(s) - regioselectivity , carborane , synthon , chemistry , ene reaction , boron , cage , surface modification , medicinal chemistry , stereochemistry , organic chemistry , catalysis , mathematics , combinatorics
1,3‐Dehydro‐o‐carborane is a useful synthon for selective cage boron functionalization of o ‐carboranes. It reacts readily with alkenes or alkynes to give a variety of cage B(3)‐alkenyl/allenyl o ‐carboranes by ene reactions in very high yields and excellent regioselectivity. This can be ascribed to the highly polarized cage CB multiple bond, which lowers the activation barriers of the ene reaction.