92076-92-1Relevant articles and documents
N-Heterocyclic Carbene Ligand-Enabled C(sp3)-H Arylation of Piperidine and Tetrahydropyran Derivatives
Ye, Shengqing,Yang, Weibo,Coon, Timothy,Fanning, Dewey,Neubert, Tim,Stamos, Dean,Yu, Jin-Quan
supporting information, p. 4748 - 4752 (2016/04/05)
PdII-catalyzed C(sp3)-H arylation of saturated heterocycles with a wide range of aryl iodides is enabled by an N-heterocyclic carbene (NHC) ligand. A C(sp3)-H insertion step by the PdII/NHC complex in the absence of ArI is demonstrated experimentally for the first time. Experimental data suggests that the previously established NHC-mediated Pd0/PdII catalytic manifold does not operate in this reaction. This transformation provides a new approach for diversifying pharmaceutically relevant piperidine and tetrahydropyran ring systems. PdII-catalyzed C(sp3)-H arylation of saturated heterocycles with a wide range of aryl iodides is enabled by an N-heterocyclic carbene (NHC) ligand. A C-H insertion step by the PdII/NHC complex in the absence of ArI is demonstrated experimentally for the first time. This arylation method provides a new approach for diversifying pharmaceutically relevant piperidine and tetrahydropyran ring systems (see scheme).