Practical access to metallo thiophenes: regioselective synthesis of 2, 4-disubstituted thiophenes

SM Asselin, MM Bio, NF Langille…

Index: Asselin, Sylvie M.; Bio, Matthew M.; Langille, Neil F.; Ngai, Ka Yi Organic Process Research and Development, 2010 , vol. 14, # 6 p. 1427 - 1431

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Citation Number: 12

Abstract

This report describes a protocol for functionalization of thiophenes, utilizing a regioselective magnesiation mediated by commercial Grignard reagents and catalytic 2, 2, 6, 6- tetramethylpiperidine. This metalation provides practical access to metallo thiophenes, avoiding cryogenic conditions, prolonged reaction times, and prohibitively expensive reagents. Application to a target thiophene-phthalazinone 6 was accomplished by ...