Transition-Metal Free C–C Bond Cross-Coupling of Aryl Ethers with Diarylmethanes

Abstract

We describe a general and efficient transition-metal free C–C bond cross-coupling of (hetero)aryl ethers and diarylmethanes via C(sp2)–O bond cleavage. The coupling reactions mediated by KHMDS proceeded well with high efficiency, broad substrate scope, and good functional group tolerance. The robustness and practicability of this protocol also have been demonstrated by easy gram-scale preparation and diversified product derivatization.

Masters of Mediation: MN(SiMe3)2 in Functionalization of C(sp3)−H Latent Nucleophiles

“…[53] Very recently, Zhao, Yang and co-workers utilized KN(SiMe 3 ) 2 as the efficient base in arylation of diarylmethanes using aryl ethers (Scheme 17). [54] They proposed that the arylation of diarylmethanes follow the formation of Meisenheimer complex, which extrudes the potassium methanolate to form the desired product 36 (Scheme 18). Only KN(SiMe 3 ) 2 found to proceed the reaction well when compared with its lighter siblings NaN(SiMe 3 ) 2 and LiN(SiMe 3 ) 2 .…”