The great potential of transition metal-catalyzed C–H functionalization is precisely selective reactions at the specific C–H bonds in complex molecules. Therefore, the development of enantio- and site-selective C–H functionalization is a long-term pursuit in this field. Herein, we disclose a ligand-enabled enantio- and site-selective remote C–H arylation of 2-(2-phenylpropyl)pyridine derivatives. The combination of an acetyl-protected aminoethyl phenyl thioether (MPA-thiol) with aryl iodides is found to enable -C(sp3)–H arylation, whereas L-pyroglutamic acid (L-pGlu) promotes the -C(sp2)–H cross-coupling with various Aryl-Bpin. Notably, both C–H arylations proceed with high enantioselectivity and good yields. The results of DFT calculation support the enantioselectivity and site-selectivity of these two C–H arylations. Moreover, the utilities of this transformation were demonstrated by derivatization of harmane alkaloid, gram-scale reaction and the successful removal of the pyridyl directing group.

You have access to this article

Please wait while we load your content... Something went wrong. Try again?