N,N-diethyl O-carbamate: directed metalation group and orthogonal Suzuki-Miyaura cross-coupling partner

Journal of the American Chemical Society
Aurora Antoft-FinchVictor Snieckus

Abstract

The first Suzuki-Miyaura cross-coupling of an aryl O-carbamate, a versatile and powerful directed metalation group (DMG) in directed ortho metalation (DoM) chemistry, is described using the inexpensive, bench-stable catalyst NiCl(2)(PCy(3))(2). Broad synthetic scope and good efficiency are demonstrated for aryl and heteroaryl O-carbamates. The role of water and hydrolysis equilibrium between free boronic acid and boroxine was established to be a crucial parameter for this transformation. When combined with DoM and traditional Pd-catalyzed Suzuki-Miyaura strategies, the methodology offers concise routes to uniquely substituted molecules, avoiding the need for protection/deprotection of the phenol and the use of strongly nucleophilic cross-coupling partners.

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Citations

Dec 8, 2010·Chemical Reviews·Brad M RosenVirgil Percec
Apr 3, 2010·Journal of the American Chemical Society·Xiaodan ZhaoVy M Dong
Apr 5, 2011·Journal of the American Chemical Society·Kyle W QuasdorfNeil K Garg
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