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Iridium(III)‐Catalyzed Selective Sulfonamidation of o ‐Carborane with Sulfonyl Azide by Carboxylic Acid‐Assisted B(4)–H Bond Activation
Author(s) -
Li Huanhuan,
Bai Fan,
Yan Hong,
Lu Changsheng,
Bregadze Vladimir I.
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601537
Subject(s) - chemistry , sulfonyl , iridium , carboxylic acid , aryl , azide , catalysis , carborane , medicinal chemistry , functional group , combinatorial chemistry , organic chemistry , alkyl , polymer
An iridium‐catalyzed cage B–H sulfonamidation of o ‐carborane directed by a carboxylic acid group is reported that proceeds in the absence of ligands or external oxidants. A series of sulfonyl azides can be selectively sulfonamidated at the B(4) site in high yields with excellent functional group tolerance. This approach can also be applied to aryl and aliphatic azides. Innocuous CO 2 and N 2 were released as byproducts. In addition, the carboxylic acid group can be easily removed under mild conditions.