PIFA-mediated oxidative cycloisomerization of 2-propargyl-1,3-dicarbonyl compounds: divergent synthesis of furfuryl alcohols and furfurals期刊界 All Journals 搜尽天下杂志传播学术成果专业期刊搜索期刊信息化学术搜索

PIFA-mediated oxidative cycloisomerization of 2-propargyl-1,3-dicarbonyl compounds: divergent synthesis of furfuryl alcohols and furfurals

Authors:	Akio Saito Toshiyuki AnzaiAsami Matsumoto Yuji Hanzawa

Affiliation:	Laboratory of Organic Reaction Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo 194-8543, Japan

Abstract:	PhI(OCOCF₃)₂ (PIFA) in the presence of trifluoroacetic acid (TFA) in CH₂Cl₂ efficiently promotes the oxidative cycloisomerization of 2-propargyl 1,3-dicarbonyl compounds to give 4,5-disubstituted furfuryl alcohols. PIFA in hexafluoroisopropanol (HFIP) or PIFA-BF₃·OEt₂ in CH₂Cl₂ bring about the direct formation of furfurals from 2-propargyl 1,3-dicarbonyl compounds. In a few cases, PhIO is suitable for the direct formation of furfurals.

Keywords:	Oxidative cycloisomerization Hypervalent iodine oxidant Furfuryl alcohol Furfural Alkynyl ketone
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