Thiol ester-boronic acid coupling. A mechanistically unprecedented and general ketone synthesis

LS Liebeskind, J Srogl

Index: Liebeskind; Srogl Journal of the American Chemical Society, 2000 , vol. 122, # 45 p. 11260 - 11261

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Citation Number: 344

Abstract

Highly discriminating activation of a stable carbon-sulfur bond is achieved in the presence of a vast sea of oxygen and nitrogen heteroatoms in various biochemical transformations. 1, 2 The Principle of Hard-Soft Acids and Bases, 3 eg, the selective interaction of a soft substrate with a soft activator in a hard environment and vice versa, helps to rationalize Nature's use of biologically relevant thiophilic metals such as Ni to achieve selective disconnection of the ...