铜（I）催化的多组分反应为全取代噻吩衍生物提供了一种新的合成方法。

Copper(I)-catalyzed multicomponent reaction providing a new access to fully substituted thiophene derivatives.

作者信息

Jiang Bo, Tu Xing-Jun, Wang Xue, Tu Shu-Jiang, Li Guigen

机构信息

School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University , Xuzhou, 221116, Jiangsu P. R. China.

出版信息

Org Lett. 2014 Jul 18;16(14):3656-9. doi: 10.1021/ol501404x. Epub 2014 Jul 2.

DOI:10.1021/ol501404x

PMID:24988049

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4337423/

Abstract

Readily available triethylammonium 1-(2-oxoindolin-3-ylidene)-2-aroylethanethiolates are efficiently converted into a variety of fully substituted thiophene derivatives by copper(I)-catalyzed denitrogenative reactions with terminal alkynes and N-sulfonyl azides. This new reaction simultaneously installs C-N, C-S, and C-C bonds, allowing direct formation of highly functionalized thiophenes with a wide diversity in substituents in a one-pot manner. A plausible mechanism for the domino process is proposed.

摘要

readily可得的三乙铵1-(2-氧代吲哚啉-3-亚基)-2-芳酰基乙硫醇盐通过与末端炔烃和N-磺酰基叠氮化物的铜(I)催化脱氮反应有效地转化为各种完全取代的噻吩衍生物。这种新反应同时形成C-N、C-S和C-C键，能够以一锅法直接形成具有广泛取代基多样性的高度官能化噻吩。提出了多米诺过程的合理机制。