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J Org Chem ; 80(6): 3176-86, 2015 Mar 20.
Article in English | MEDLINE | ID: mdl-25763683

ABSTRACT

PdCl2(CH3CN)2-catalyzed arylation of unactivated C(sp(3))-H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp(3))-H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.


Subject(s)
Carbonates/chemistry , Cesium/chemistry , Organometallic Compounds/chemistry , Palladium/chemistry , Psychotropic Drugs/chemical synthesis , gamma-Aminobutyric Acid/analogs & derivatives , Catalysis , Molecular Structure , Psychotropic Drugs/chemistry , gamma-Aminobutyric Acid/chemical synthesis , gamma-Aminobutyric Acid/chemistry
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