New cyclopalladated benzothiophenes: a catalyst precursor for the Suzuki coupling of deactivated aryl chlorides.
Dimeric benzothiophene-based palladacycles were synthesized from thioanisole-substituted perfluoroalkyl propargyl imines and palladium(II) salts via an intramolecular thiopalladation pathway. The treatment of benzothiophene-based palladacycles with an excess of phosphine ligands in benzene at room temperature selectively afforded trans-bis(phosphine) palladium complexes in good yields. The trans-bis(tricyclohexylphosphine) palladium complex was found to be an active catalyst in the Suzuki coupling of electron rich aryl chlorides. The complex was also employed in the catalytic synthesis of sterically hindered biaryls. The anticancer activity of palladacycles is also discussed.
Subhas
Madavu Salian
MS
Inorganic and Physical Chemistry Division, Indian Institute Chemical Technology, Uppal Road, Tarnaka, Hyderabad, 500670, India.
Racharlawar
Shailesh S
SS
Sridhar
B
B
Kennady
P Kavin
PK
Likhar
Pravin R
PR
Kantam
Mannepalli Lakshmi
ML
Bhargava
Suresh K
SK
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D017209:Apoptosis / Q000187:drug effects; D002384:Catalysis; D045744:Cell Line, Tumor; D002463:Cell Membrane Permeability / Q000187:drug effects; D002713:Chlorine / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D009942:Organometallic Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010165:Palladium / Q000737:chemistry*; D013876:Thiophenes / Q000737:chemistry*
D000970:Antineoplastic Agents; D009942:Organometallic Compounds; D013876:Thiophenes; C088015:benzothiophene; D002713:Chlorine; D010165:Palladium