92076-92-1Relevant academic research and scientific papers
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).
Friedel-Crafts Acylation with N-(Trifluoroacetyl)-α-amino Acid Chlorides. Application to the Preparation of β-Arylalkylamines and 3-Substituted 1,2,3,4-Tetrahydroisoquinolines
Nordlander, Eric J.,Payne, Mark J.,Njoroge, George F.,Balk, Michael A.,Laikos George D.,Vishwanath, Vasanth M.
, p. 4107 - 4111 (2007/10/02)
Several N-(trifluoroacetyl)-α-amino acid chlorides have been reacted with benzene, anisole, and veratrole in the presence of AlCl3 or SnCl4 to produce the corresponding aromatic ketones in fair to high yields.The products are reductible under neutral or acidic conditions to the corresponding N-(trifluoroacetyl)-β-hydroxy-β-arylakylamines or N-(trifluoroacetyl)-β-arylalkylamines.The latter can be readily detrifluoroacetylated by mild basic hydrolysis and thence converted to the corresponding 3-substituted 1,2,3,4-tetrahydroisoquinolines by condensation with formaldehyde.
