Issue 18, 2022

Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1,6-diynes

Abstract

A highly regio- and chemoselective synthesis of 1H-isoindoliums through a facile and novel cascade cyclization reaction of propargylamine-based 1,6-diynes under mild conditions has been developed. Different functional groups were compatible under the optimized reaction conditions, giving the corresponding products in up to 94% yields. Upon treatment with a base, the alkyne moiety of 1H-isoindoliums could be further transformed to allenes in excellent yields.

Graphical abstract: Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1,6-diynes

Supplementary files

Article information

Article type
Paper
Submitted
15 Feb 2022
Accepted
06 Apr 2022
First published
07 Apr 2022

Org. Biomol. Chem., 2022,20, 3755-3762

Synthesis of 1H-isoindoliums by electrophile-mediated cascade cyclization/iodination of propargylamine-based 1,6-diynes

J. Cui, Q. Yu, W. O, L. Huang, B. Yang and M. Wong, Org. Biomol. Chem., 2022, 20, 3755 DOI: 10.1039/D2OB00316C

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