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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Bibliographic Details
Published inOrganic process research & development Vol. 14; no. 1; pp. 180 - 187
Main Authors Berliner, Martin A, Cordi, Eric M, Dunetz, Joshua R, Price, Kristin E
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 15.01.2010
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Applied
Chemistry, Organic
Physical Sciences
Science & Technology
SUZUKI
OLEFINS
VERSATILE
ANALOGS
DERIVATIVES
CATALYZED SYNTHESIS
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Summary: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.
ISSN:1083-6160
1520-586X
DOI:10.1021/op900263b