Tetrahedron

A chemoselective Reformatsky–Negishi approach to α-haloaryl esters

B Wong, X Linghu, JJ Crawford, J Drobnick, W Lee…

Index: Wong, Brian; Linghu, Xin; Crawford, James J.; Drobnick, Joy; Lee, Wendy; Zhang, Haiming Tetrahedron, 2014 , vol. 70, # 7 p. 1508 - 1515

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Citation Number: 4

Abstract

Abstract A practical synthesis of α-haloaryl esters has been achieved via a chemoselective Negishi coupling of poly-halogenated aromatics and Reformatsky reagents in the presence of catalytic Pd (dba) 2 and Xantphos. This chemistry tolerates a variety of aryl halides and was successfully applied to the synthesis of Ibuprofen. The α-haloaryl ester products, exemplified by ethyl 2-(4-bromo-2-chlorophenyl) acetate (3a), can be further ...