N‐Heterocyclic Carbene Ligand‐Enabled C(sp3)−H Arylation of Piperidine and Tetrahydropyran Derivatives. Issue 14 (24th February 2016)

• Record Type: Journal Article
• Authors: Ye, Shengqing; Yang, Weibo; Coon, Timothy; Fanning, Dewey; Neubert, Tim; Stamos, Dean; Yu, Jin‐Quan
• Is Part Of: Chemistry. Volume 22:Issue 14(2016)
• Page Start: 4748
• Page End: 4752
• Publication Date: 2016-02-24
• Subjects: arylation -- C−H activation -- heterocycles -- N-heterocyclic carbenes -- palladium; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201600191
• Languages: English
• ISSNs: 0947-6539

Abstract

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. 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−H insertion step by the Pd II /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).