Tetrahedron letters

Preparation of N-hydroxysuccinimido esters via palladium-catalyzed carbonylation of aryl triflates and halides

R Lou, M VanAlstine, X Sun, MP Wentland

Index: Lou, Rongliang; VanAlstine, Melissa; Sun, Xufeng; Wentland, Mark P. Tetrahedron Letters, 2003 , vol. 44, # 12 p. 2477 - 2480

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Citation Number: 26

Abstract

N-Hydroxysuccinimido esters of aromatic carboxylic acids (aka active esters) can be made using a potentially general, one-step procedure via Pd-catalyzed carbonylation of an aryl triflate or aryl iodide with CO and N-hydroxysuccinimide. Excellent yields (up to 94%) were observed when the reaction was done in DMSO at 70° C and 1 atmosphere of CO pressure.

~74%

~88%

~69%

~25%

~64%

~62%

~86%

~90%

~83%

~87%

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