Sonogashira Reactions with Propyne: Facile Synthesis of 4-Hydroxy-2-methylbenzofurans from Iodoresorcinols

The Sonogashira reaction of terminal alkynes and ortho-halophenols with subsequent cyclization is a well-precedented method for the synthesis of substituted benzofurans. Here we describe the extension of this method to the coupling of 2-iodoresorcinols and terminal alkynes, including propyne, to giv...

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Veröffentlicht in:	Organic process research & development 2010-01, Vol.14 (1), p.180-187
Hauptverfasser:	Berliner, Martin A, Cordi, Eric M, Dunetz, Joshua R, Price, Kristin E
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Sprache:	eng
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creator	Berliner, Martin A Cordi, Eric M Dunetz, Joshua R Price, Kristin E
description	The Sonogashira reaction of terminal alkynes and ortho-halophenols with subsequent cyclization is a well-precedented method for the synthesis of substituted benzofurans. Here we describe the extension of this method to the coupling of 2-iodoresorcinols and terminal alkynes, including propyne, to give 4-hydroxy-2-substituted benzofurans. In particular, we describe the screening, method development, and scaleup of the reaction with propyne using standard hydrogenation equipment.
doi_str_mv	10.1021/op900263b
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title	Sonogashira Reactions with Propyne: Facile Synthesis of 4-Hydroxy-2-methylbenzofurans from Iodoresorcinols
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