Thiol on silica as a 'catch and release'support for isocyanates to afford ureas

Y Bolshan, MJ Tomaszewski, V Santhakumar

Index: Bolshan, Yuri; Tomaszewski, Miroslaw J.; Santhakumar, Vijayaratnam Tetrahedron Letters, 2007 , vol. 48, # 28 p. 4925 - 4927

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Citation Number: 11

Abstract

Silica-bound thiocarbamates were prepared by Curtius rearrangement of carboxylic acids in the presence of thiol on silica gel. The solid supported thiocarbamates were found to be stable isocyanate equivalents, which upon treatment with amines efficiently afforded di-and tri-substituted ureas. The urea products released from the catch and release support were, in the majority of cases, greater than 95% pure and required no further work up.