Issue 34, 2017

Palladium-catalyzed tandem cyclization/sulfonylation of homoallenyl amides with sodium sulfinates

Abstract

A palladium-catalyzed cyclizative sulfonylation of homoallenyl amides using sodium sulfinates as the sulfonylation reagent and PhI(O2CCF3)2 as the oxidant has been realized. The reaction proceeds at room temperature and produces structurally diverse 2-amino-5-sulfonylmethylfurans in good to excellent yields. A Pd(II)/Pd(IV) catalytic cycle has been proposed for the formation of sulfonylated furans. The concurrent formation of a furan moiety and a C(sp3)–sulfur bond in a single operation makes it a very attractive method for organic synthesis.

Graphical abstract: Palladium-catalyzed tandem cyclization/sulfonylation of homoallenyl amides with sodium sulfinates

Supplementary files

Article information

Article type
Paper
Submitted
02 Aug 2017
Accepted
11 Aug 2017
First published
11 Aug 2017

Org. Biomol. Chem., 2017,15, 7204-7211

Palladium-catalyzed tandem cyclization/sulfonylation of homoallenyl amides with sodium sulfinates

Y. Wan, J. Zhang, Y. Chen, L. Kong, F. Luo and G. Zhu, Org. Biomol. Chem., 2017, 15, 7204 DOI: 10.1039/C7OB01922J

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements