68587-18-8Relevant academic research and scientific papers
Palladium-catalyzed approach for the general synthesis of (E)-2-arylmethylidene-N-tosylindolines and (E)-2-arylmethylidene-N-tosyl/ nosyltetrahydroquinolines: Access to 2-substituted indoles and quinolines
Chowdhury, Chinmay,Das, Bimolendu,Mukherjee, Sanjukta,Achari, Basudeb
, p. 5108 - 5119 (2012/07/14)
A facile and efficient method for the synthesis of (E)-2-arylmethylidene-N- tosylindolines and (E)-2-arylmethylidene-N-tosyl/nosyltetrahydroquinoline variants has been developed through palladium-catalyzed cyclocondensation of aryl iodides with readily available 1-(2-tosylaminophenyl)prop-2-yn-1-ols and their higher homologues, respectively. The proposed reaction mechanism invokes the operation of trans-aminopalladation during cyclization (5/6-exo-dig), which ensures exclusive (E)-stereochemistry in the products. The method is fast, operationally simple, totally regio- and stereoselective, and versatile enough to access a variety of 2-substituted indoles and quinolines. The reactions proceeded efficiently with a wide variety of substrates and afforded the corresponding products in moderate to excellent yields.
