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Transition Metal Catalyzed, Regioselective B (4)‐Halogenation and B (4,5)‐Diiodination of Cage B−H Bonds in o ‐Carboranes
Author(s) -
Lyu Hairong,
Quan Yangjian,
Xie Zuowei
Publication year - 2017
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.201703006
Subject(s) - halogenation , regioselectivity , synthon , chemistry , catalysis , cage , carborane , transition metal , medicinal chemistry , selectivity , stereochemistry , organic chemistry , mathematics , combinatorics
Abstract Transition metal catalyzed, regioselective carborane‐cage B (4)−H iodination, bromination, and chlorination as well as B (4,5)−H diiodination were achieved by using NXS (X=I, Br), FeCl 3 , or IOAc as the halogenating agent, respectively. A series of previously inaccessible B (4)‐halogenated o ‐carboranes were synthesized in a simple one‐pot process, and proved to be valuable synthons for the functionalization of carboranes. Mono‐ and di‐selectivity can be controlled by in situ removal of the carboxy directing group. The resultant 4‐I‐ o ‐C 2 B 10 H 11 can serve as a versatile feedstock for the construction of cage B−C(sp 2 ), B−C(sp), B−O, and B−N bonds.

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