文献类型：期刊文献

英文题名：Bifunctional Phosphine Ligand Enabled Gold-Catalyzed Alkynamide Cycloisomerization: Access to Electron-Rich 2-Aminofurans and Their Diels-Alder Adducts

作者：Li, Xingguang[1,2,3];Ma, Xu[1];Wang, Zhixun[1];Liu, Pei-Nian[2,3];Zhang, Liming[1]

机构：[1]Univ Calif Santa Barbara, Dept Chem & Biochem, Santa Barbara, CA 93106 USA;[2]East China Univ Sci & Technol, Shanghai Key Lab Funct Mat Chem, Key Lab Adv Mat, Meilong Rd 130, Shanghai 200237, Peoples R China;[3]East China Univ Sci & Technol, Inst Fine Chem, Meilong Rd 130, Shanghai 200237, Peoples R China

年份：2019

卷号：58

期号：48

起止页码：17180

外文期刊名：ANGEWANDTE CHEMIE-INTERNATIONAL EDITION

收录：;EI(收录号：20194407606329);WOS:【SCI-EXPANDED(收录号:WOS:000492256000001)，CCR-EXPANDED(收录号:WOS:000492256000001)】；

基金：We thank the NSF (CHE 1800525) and NIGMS (R01GM123342) for generous financial support and the NIH shared instrument grant S10OD012077 for the purchase of a 400MHz NMR spectrometer. ZW thanks the Mellichamp Academic Initiative in Sustainability for a fellowship in support of his research.

语种：英文

外文关键词：dienes; Diels-Alder reactions; gold; heterocycles; isomerizations

摘要：By using biphenyl-2-ylphosphines functionalized with a remote tertiary amino group as a ligand, readily available acetylenic amides are directly converted into 2-aminofurans devoid of any electron-withdrawing and hence deactivating/stabilizing substituents. These highly electron-rich furans have rarely been prepared, let alone applied in synthesis, because of their high reactivities and low stabilities associated with the electron-rich nature of the furan ring. In this work, these reactive furans smoothly undergo either in situ intermolecular Diels-Alder reactions to deliver highly functionalized/substituted aniline products or intramolecular ones to furnish carbazole-4-carboxylates in mostly good to excellent yields. This work offers general and expedient access to this class of little studies electron-rich furans and should lead to exciting opportunities for their applications.