Synthesis of Fully Substituted 3-Formyl-4-iodofurans via a Gold(I)-Catalyzed Oxidation/1,2-Alkynyl Migration/Cyclization/Iodination Cascade

被引：84
|
作者：
Wang, Tao [1 ]
Shi, Shuai [1 ]
Rudolph, Matthias [1 ]
Hashmi, A. Stephen K. [1 ,2 ]
机构：
[1] Heidelberg Univ, Inst Organ Chem, D-69120 Heidelberg, Germany
[2] King Abdulaziz Univ, Dept Chem, Fac Sci, Jeddah 21589, Saudi Arabia
来源：
ADVANCED SYNTHESIS & CATALYSIS | 2014年 / 356卷 / 10期
关键词：
alkynes; furans; gold; iodine; N-oxides; GOLD-CATALYSIS; OXIDATIVE REARRANGEMENT; ORGANOGOLD COMPOUNDS; EFFICIENT SYNTHESIS; N-HALOSUCCINIMIDES; ALKYNES; FURANS; FUNCTIONALIZATION; CYCLIZATION; CARBENOIDS;
D O I：
10.1002/adsc.201400356
中图分类号：
O69 [应用化学];
学科分类号：
081704 ;
摘要：
A highly efficient gold(I)-catalyzed cascade reaction for the synthesis of fully substituted 3-formyl-4-iodofurans has been developed. Mechanistic investigations indicate a reaction pathway that involves a direct iodination reaction of the organogold intermediate via functionalization of the Au-C(sp(2)) bond, instead of a direct iodination of the 3-formylfurans.
引用
收藏
页码：2337 / 2342
页数：6
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