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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

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Title 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
 
Creator Chowdhury, Chinmay
Das, Bimolendu
Mukherjee, Sanjukta
Achari, Basudeb
 
Subject Chemistry
 
Description 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.
 
Publisher American Chemical Society
 
Date 2012
 
Type Article
PeerReviewed
 
Format application/pdf
 
Identifier http://www.eprints.iicb.res.in/1535/1/OURNAL_OF_ORGANIC_CHEMISTRY__77__(_11)__5108%2D5119;2012[5].pdf
Chowdhury, Chinmay and Das, Bimolendu and Mukherjee, Sanjukta and Achari, Basudeb (2012) 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. The Journal of Organic Chemistry, 77 (11). pp. 5108-5119.
 
Relation http://dx.doi.org/dx.doi.org/10.1021/jo300458v
http://www.eprints.iicb.res.in/1535/