Palladium-catalyzed cross-coupling of five-membered heterocyclic silanolates

SE Denmark, JD Baird, CS Regens

Index: Denmark, Scott E.; Baird, John D.; Regens, Christopher S. Journal of Organic Chemistry, 2008 , vol. 73, # 4 p. 1440 - 1455

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Citation Number: 68

Abstract

The preparation of π-rich 2-aryl heterocycles by palladium-catalyzed cross-coupling of sodium heteroarylsilanolates with aryl iodides, bromides, and chlorides is described. The cross-coupling process was developed through extensive optimization of the following key variables:(1) identification of stable, isolable alkali metal silanolates,(2) identification of conditions for preformation and isolation of silanolate salts,(3) judicious choice in the ...