Pd(ii)-catalyzed alkoxylation of unactivated C(sp3)–H and C(sp2)–H bonds using a removable directing group: efficient synthesis of alkyl ethers

Abstract

The Pd(II)-catalyzed alkoxylation of unactivated C(sp3)–H and C(sp2)–H bonds using a new bidentate directing group has been developed. Alkoxylation occurs selectively at the β position with broad substrate scope and high tolerance of functional groups (chloro, cyano, ether, ester, olefin, amino, etc.). Besides alkoxylation of the β-C–H bonds, γ-alkoxylation of C(sp2)–H bonds could also be achieved, provided that no reactive β-C–H bonds were present. In addition, this DG is readily available and removable.