Issue 1, 2017

Synthesis of polycyclic sultams via a palladium-catalyzed reaction of 1-bromo-2-(cyclopropylidenemethyl)benzenes with 2-alkynylbenzenesulfonamides

Abstract

Polycyclic sultams are efficiently synthesized through a palladium-catalyzed tandem reaction of 1-bromo-2-(cyclopropylidenemethyl)benzenes with 2-alkynylbenzenesulfonamides. The transformation proceeds through double carbometallation with excellent chemoselectivity and regioselectivity, leading to a range of 7,7a-dihydro-6H-benzo[f]indeno[1,2-d][1,2]thiazepine 5,5-dioxides in moderate to good yields. During the reaction process, three new bonds and two rings including the seven-membered sultam ring are formed.

Graphical abstract: Synthesis of polycyclic sultams via a palladium-catalyzed reaction of 1-bromo-2-(cyclopropylidenemethyl)benzenes with 2-alkynylbenzenesulfonamides

Supplementary files

Article information

Article type
Research Article
Submitted
22 Aug 2016
Accepted
25 Oct 2016
First published
26 Oct 2016

Org. Chem. Front., 2017,4, 14-17

Synthesis of polycyclic sultams via a palladium-catalyzed reaction of 1-bromo-2-(cyclopropylidenemethyl)benzenes with 2-alkynylbenzenesulfonamides

X. Gong, G. Li and J. Wu, Org. Chem. Front., 2017, 4, 14 DOI: 10.1039/C6QO00480F

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