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

被引：24
|
作者：
Saito, Akio [1 ]
Anzai, Toshiyuki [1 ]
Matsumoto, Asami [1 ]
Hanzawa, Yuji [1 ]
机构：
[1] Showa Pharmaceut Univ, Lab Organ React Chem, Tokyo 1948543, Japan
来源：
TETRAHEDRON LETTERS | 2011年 / 52卷 / 36期
关键词：
Oxidative cycloisomerization; Hypervalent iodine oxidant; Furfuryl alcohol; Furfural; Alkynyl ketone; HIGHLY SUBSTITUTED FURANS; PALLADIUM-CATALYZED CYCLIZATION; MULTISUBSTITUTED 2-ACYL FURANS; AMINO-CLAISEN REARRANGEMENT; ONE-POT SYNTHESIS; 1,3-DICARBONYL COMPOUNDS; TETRASUBSTITUTED FURANS; ALKYNE AMIDATION; DOMINO PROCESS; CHEMISTRY;
D O I：
10.1016/j.tetlet.2011.06.117
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 center dot OEt\(2) in CH2Cl2 bring about the direct formation of furfurals from 2-propargyl 1,3-dicarbonyl compounds. In a few cases, PhI=O is suitable for the direct formation of furfurals. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4658 / 4661
页数：4
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