羰基官能团与炔烃串联反应中的银催化与金催化：通往呋喃喹啉和吡喃喹啉核心结构的通用方法

Silver versus gold catalysis in tandem reactions of carbonyl functions onto alkynes: a versatile access to furoquinoline and pyranoquinoline cores.

作者信息

Godet Thomas, Vaxelaire Carine, Michel Carine, Milet Anne, Belmont Philippe

机构信息

Institut de Chimie et Biochimie Moléculaires et Supramoléculaires, ICBMS, Université Claude Bernard, Lyon I. UMR CNRS 5246, Bâtiment CPE, 43 boulevard du 11 Novembre 1918, 69622 Villeurbanne cedex, France.

出版信息

Chemistry. 2007;13(19):5632-41. doi: 10.1002/chem.200700202.

DOI:10.1002/chem.200700202

PMID:17361970

Abstract

An efficient and versatile tandem process of acetalization and cycloisomerization reactions has been developed for the reactions of 1-alkynyl-2-carbonylquinoline substrates. The reaction occurs thanks to Au(I) and Ag(I) catalysis. Silver(I) catalysis has been extensively studied (11 different silver species) on a broad range of quinoline derivatives (variation of alkyne substituent, of carbonyl function and of nucleophiles), leading to a variety of furoquinoline and pyranoquinoline moieties. An insight is given for the presumed mechanism along with DFT-B3 LYP/6-31G** calculations to address the 6-endo and 5-exo regioselectivities observed.

摘要

针对1-炔基-2-羰基喹啉底物的反应，开发了一种高效且通用的缩醛化和环异构化串联反应过程。该反应在金（I）和银（I）催化下发生。银（I）催化已在广泛的喹啉衍生物（炔烃取代基、羰基官能团和亲核试剂的变化）上进行了广泛研究（11种不同的银物种），生成了多种呋喃并喹啉和吡喃并喹啉部分。同时给出了推测机理的见解以及DFT-B3 LYP/6-31G**计算结果，以解释所观察到的6-内型和5-外型区域选择性。