Journal
CHINESE JOURNAL OF CHEMISTRY
Volume 38, Issue 4, Pages 383-388Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/cjoc.201900475
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Funding
- Research Grants Council of The Hong Kong Special Administration Region [14305017, 14305018, 14305918]
- Faculty of Science, CUHK
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Ir-catalyzed cascade dehydrogenative CH/BH and BH/OH cross-coupling of carboranyl carboxylic acid with readily available benzoic acid has been achieved, leading to the facile synthesis of previously unavailable carborano-coumarin in a simple one-pot process. Two cage B-H, one aryl C-H and one O-H bonds are activated to construct efficiently new B-C and B-O bonds. The cascade cyclization can stop at the first B-H/C-H cross-coupling step by tuning the reaction conditions, resulting in a series of alpha-carboranyl benzoic acid and aryl carborane derivatives. Control experiments indicate that B-H/C-H dehydrocoupling proceeds preferentially over B-H/O-H dehydrocoupling, and both directing groups and oxidants are crucial for this reaction. An iridium(V) intermediate is proposed to be involved in the catalytic cycle.
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