Journal
ORGANIC LETTERS
Volume 19, Issue 22, Pages 6136-6139Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.7b03016
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- Council of Scientific and Industrial Research (CSIR), New Delhi
- BRNS, Mumbai
- SERB, New Delhi
- IRCC, IIT Bombay
- UGC, New Delhi
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An efficient protocol for the stereoselective synthesis of benzo[1,4]heterocycles via palladium catalyzed Heck reaction, on o-halo-aryl-oxa/thia/aza tethered vinylogous carbonates/carbamates/esters has been developed. Unexpected formation; of indoles is observed when unprotected 2-iodoariiline tethered Vinylogous carbonates are subjected to the Heck reaction. Mechanistic studies indicate that formation of these indoles is an outcome of the interception of the carbopalladation step by nucleopalladation. The method can be used to gain rapid access to the core skeleton of abacopterin A-C.
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