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Thiophosphoramide‐Based Cooperative Catalysts for Brønsted Acid Promoted Ionic Diels–Alder Reactions
Author(s) -
Borovika Alina,
Tang PuiIn,
Klapman Seth,
Nagorny Pavel
Publication year - 2013
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201307133
Subject(s) - counterion , catalysis , chemistry , ionic bonding , hydrogen bond , brønsted–lowry acid–base theory , ionic liquid , medicinal chemistry , hydrogen , polymer chemistry , organic chemistry , ion , molecule
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.