Premium
N‐Heterocyclic Carbene Ligand‐Enabled C(sp 3 )−H Arylation of Piperidine and Tetrahydropyran Derivatives
Author(s) -
Ye Shengqing,
Yang Weibo,
Coon Timothy,
Fanning Dewey,
Neubert Tim,
Stamos Dean,
Yu JinQuan
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201600191
Subject(s) - carbene , tetrahydropyran , piperidine , ligand (biochemistry) , chemistry , ring (chemistry) , aryl , medicinal chemistry , catalysis , stereochemistry , combinatorial chemistry , organic chemistry , receptor , biochemistry , alkyl
Abstract Pd II ‐catalyzed C(sp 3 )−H arylation of saturated heterocycles with a wide range of aryl iodides is enabled by an N‐heterocyclic carbene (NHC) ligand. A C(sp 3 )−H insertion step by the Pd II /NHC complex in the absence of ArI is demonstrated experimentally for the first time. Experimental data suggests that the previously established NHC‐mediated Pd 0 /Pd II catalytic manifold does not operate in this reaction. This transformation provides a new approach for diversifying pharmaceutically relevant piperidine and tetrahydropyran ring systems.