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Room Temperature Carbonylation of (Hetero) Aryl Pentafluorobenzenesulfonates and Triflates using Palladium‐Cobalt Bimetallic Catalyst: Dual Role of Cobalt Carbonyl
Author(s) -
Joseph Jayan T.,
Sajith Ayyiliath M.,
Ningegowda Revanna C.,
Shashikanth Sheena
Publication year - 2017
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201600736
Subject(s) - carbonylation , chemistry , palladium , aryl , bimetallic strip , cobalt , catalysis , electrophile , chemoselectivity , carbon monoxide , combinatorial chemistry , photochemistry , organic chemistry , alkyl
An efficient method for the carbonylation of (hetero) aryl pentafluorobenzenesulfonates and triflates under exceptionally mild conditions using palladium/dicobalt octacarbonyl [Pd/Co 2 (CO) 8 ] has been developed. Besides acting as carbon monoxide (CO) source, Co 2 (CO) 8 enhances the reaction rate by accelerating the CO insertion through an in situ generated bimetallic palladium cobalt tetracarbonyl [Pd‐Co(CO) 4 ] complex. Under the optimized reaction condition, carbonylation of a wide range of activated and deactivated, as well as sterically hindered and heteroaromatic, substrates proceeded efficiently at room temperature. The high chemoselectivity and improved synthesis of biologically relevant Isoguvacine and Lazabemide intermediates highlights its scope as a valuable synthetic method. The generality of this protocol was further extended to other electrophiles (bromides, chlorides and tosylates).