A facile approach for the synthesis of nido-carborane fused oxazoles via one pot deboronation/cyclization of 9-amide-o-carboranes

A one pot deboronation/cyclization of 9-amide-o-carboranes for the synthesis of nido-7,8-carborane fused oxazole by cooperation of Pd(OAc)2, AgOAc and K2CO3 has been developed. A plausible mechanism involving an amide directed electrophilic palladation of the B-H bond and deboronation/cyclization pr...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2019-01, Vol.55 (6), p.830-833
Main Authors: Zhang, Cai-Yan, Cao, Ke, Xu, Tao-Tao, Wu, Ji, Jiang, Linhai, Yang, Junxiao
Format: Article
Language:English
Subjects:
Carborane
Crystallography
Hydrogen bonds
NMR
Nuclear magnetic resonance
Oxazole
Potassium carbonate
Structural analysis
Synthesis
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Summary:A one pot deboronation/cyclization of 9-amide-o-carboranes for the synthesis of nido-7,8-carborane fused oxazole by cooperation of Pd(OAc)2, AgOAc and K2CO3 has been developed. A plausible mechanism involving an amide directed electrophilic palladation of the B-H bond and deboronation/cyclization process was proposed based on the successful isolation and structural characterization of the key deboronated intermediate.
ISSN:1359-7345
1364-548X
DOI:10.1039/c8cc07728b