Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2017, Issue 10, Pages 1343-1352Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201601537
Keywords
B-H activation; Iridium; Sulfonamidation; Azides; Regioselectivity
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Funding
- National Natural Science Foundation of China [21271102, 21472086, 21531004]
- China-Russia joint grant (RFBR) [16-53-53079, 21611130027]
- National Basic Research Program of China [2013CB922101]
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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 CO2 and N-2 were released as byproducts. In addition, the carboxylic acid group can be easily removed under mild conditions.
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