4 years ago

Silyloxyarenes as Versatile Coupling Substrates Enabled by Nickel-Catalyzed C–O Bond Cleavage

Silyloxyarenes as Versatile Coupling Substrates Enabled by Nickel-Catalyzed C–O Bond Cleavage
David P. Todd, John Montgomery, Eric M. Wiensch
Silyloxyarenes are demonstrated to be a versatile substrate class in a variety of nickel-catalyzed coupling processes. The C(sp2)–O bond of aryl silyl ethers is directly transformed into C–H or C–Si bonds using Ti(O-i-Pr)4 or trialkylsilanes as reagents using nickel catalysts with N-heterocyclic carbene (NHC) ligands. Paired with the useful characteristics of silyl protecting groups, these methods enable protected hydroxyls to directly participate in high-value bond-forming steps rather than requiring deprotection-activation strategies that conventional approaches require. These processes of silyloxyarenes provide reactivity complementary to widely used phenol derivatives such as aryl pivalates, carbamates, and methyl ethers, thus enabling a powerful strategy for sequential chemoselective derivatization of complex substrates without protecting group and activating group manipulations.

Publisher URL: http://dx.doi.org/10.1021/acscatal.7b02025

DOI: 10.1021/acscatal.7b02025

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