Tetrahedron Letters

An efficient synthesis of a class of heterobifunctional photo-reactive crosslinkers, labels, and probes

KW Gano, HG Monbouquette, DC Myles

Index: Gano, Kyle W.; Monbouquette, Harold G.; Myles, David C. Tetrahedron Letters, 2001 , vol. 42, # 12 p. 2249 - 2251

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Citation Number: 11

Abstract

Aryl esters are selectively reduced with DIBAL-H in the presence of an azide functional group to provide access to 4-azido-2-alkoxybenzaldehydes in five steps with overall yields ranging from 72 to 78%. This methodology improves traditional approaches to this class of compounds, which suffer from poor overall yields (4–11%). Our approach can be used to synthesize a variety of new aryl azide cross-linkers, labels, and probes.