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

The Pd(II)-catalyzed alkoxylation of unactivated C(sp(3))-H and C(sp(2))-H bonds using a new bidentate directing group has been developed. Alkoxylation occurs selectively at the beta position with broad substrate scope and high tolerance of functional groups (chloro, cyano, ether, ester, olefin, amino, etc.). Besides alkoxylation of the beta-C-H bonds, gamma-alkoxylation of C(sp(2))-H bonds could also be achieved, provided that no reactive beta-C-H bonds were present. In addition, this DG is readily available and removable.