Stepwise iododesilylation and coupling reaction: a flexible route to 2, 4-disubstituted-1H-pyrroles. Issue 23 (8th June 2016)

• Record Type: Journal Article
• Authors: Liu, Jianhui; Fu, Nanyan; Wei, Changyun; Song, Zhucao
• Is Part Of: Tetrahedron letters. Volume 57:Issue 23(2016)
• Page Start: 2530
• Page End: 2532
• Publication Date: 2016-06-08
• Subjects: 2, 4-Disubstituted pyrroles -- Iododesilylation -- Suzuki coupling reaction -- TMS-migration; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.04.105
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A new strategy for the synthesis of 2, 4-disubstituted pyrroles. A stepwise iododesilylation and palladium-catalysed Suzuki coupling reaction. Regioselective iododesilylation can be achieved under simple and mild conditions. Abstract: In this study, we report a new strategy for the synthesis of 2, 4-disubstituted pyrroles using a stepwise iododesilylation and palladium-catalysed Suzuki coupling reaction of 2, 4-bis(trimethylsilyl)-1- t -Boc-1 H -pyrrole (2 ). The regioselective iodo-desilylation followed by the Suzuki coupling reaction with concomitant Boc deprotection are critical aspects of the new synthesis method.