通过铜催化的串联芳基化-缩合过程简便合成多取代吲哚。

Facile access to polysubstituted indoles via a cascade Cu-catalyzed arylation-condensation process.

作者信息

Chen Yu, Xie Xiaoan, Ma Dawei

机构信息

Department of Chemistry, Fudan University, Shanghai, China.

出版信息

J Org Chem. 2007 Nov 23;72(24):9329-34. doi: 10.1021/jo702059q. Epub 2007 Nov 2.

DOI:10.1021/jo702059q

PMID:17975934

Abstract

Cu(I)/L-proline-catalyzed cross-coupling of 2-halotrifluoroacetanilides with beta-keto esters and amides followed by in situ acidic hydrolysis delivered 2,3-disubstituted indoles. The halides bearing a strong electron-withdrawing group in the 4-position can undergo in situ basic hydrolysis to provide the corresponding indoles. Polysubstituted indoles can be prepared from substituted 2-halotrifluoroacetanilides with high regioselectivity.

摘要

铜（I）/L-脯氨酸催化的2-卤代三氟乙酰苯胺与β-酮酯和酰胺的交叉偶联反应，随后进行原位酸水解，得到2,3-二取代吲哚。在4-位带有强吸电子基团的卤化物可进行原位碱水解，以提供相应的吲哚。多取代吲哚可由取代的2-卤代三氟乙酰苯胺以高区域选择性制备。