N-heterocyclic carbene–palladium(ii)-1-methylimidazole complex-catalyzed Suzuki–Miyaura coupling of benzyl sulfonates with arylboronic acids?

Organic & Biomolecular Chemistry Pub Date: 2015-03-19 DOI: 10.1039/C4OB02675F

Abstract

The first example of palladium-catalyzed Suzuki–Miyaura coupling between benzyl sulfonates and arylboronic acids was reported in this paper. In the presence of a well-defined, air-stable and easily available NHC–Pd(II)–Im complex, all reactions worked well to give the desired products in good to almost quantitative yields under the optimal conditions. Electron-rich, -neutral, -poor and sterically-hindered substituents on both substrates are tolerated in such transformation, providing a convenient, efficient and alternative method for the synthesis of diarylmethanes.

Graphical abstract: N-heterocyclic carbene–palladium(ii)-1-methylimidazole complex-catalyzed Suzuki–Miyaura coupling of benzyl sulfonates with arylboronic acids
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