Monday, October 21, 2013

Thiophosphoramide-Based Cooperative Catalysts for Brønsted Acid Promoted Ionic Diels–Alder Reactions

by Alina Borovika, Pui-In Tang, Seth Klapman, Pavel Nagorny*

Thumbnail image of graphical abstract


Three's a crowd: The combination of a Brønsted acid and a hydrogen-bond donor cocatalyst was found to promote various ionic [2+4] cycloadditions under mild reaction conditions (see scheme; Ts=4-toluenesulfonyl). Thiophosphoramides are the most effective cocatalysts because of the stronger counterion activation effect resulting from three, rather than two, hydrogen bonds involved in anion binding.


Angewandte Chemie International Edition

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