1021176-10-2Relevant academic research and scientific papers
Synthesis of fluorenes via the palladium-catalyzed 5-exo-dig annulation of o-alkynylbiaryls
Chernyak, Natalia,Gevorgyan, Vladimir
experimental part, p. 1101 - 1114 (2009/12/07)
The direct palladium-catalyzed intramolecular hydro arylation of o-alkynylbiaryls proceeded in a highly stereoselective manner producing fluorenes 2, the products of 5-exo-dig cyclization, in excellent yields. The cascade intermolecular arylation, incorpo
Exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls proceeding via C-H activation pathway
Chernyak, Natalia,Gevorgyan, Vladimir
, p. 5636 - 5637 (2008/12/22)
The first example of the palladium-catalyzed exclusive 5-exo-dig hydroarylation of o-alkynyl biaryls has been demonstrated. In contrast to the reported earlier carbocyclizations proceeding via the Friedel-Crafts mechanism, this hydroarylation efficiently proceeds with electron-neutral and electron-deficient arenes, producing fluorene frameworks with defined stereochemistry of the double bond. On the basis of the high reactivity of electron-deficient arenes toward cyclization, high values of inter- and intramolecular kinetic isotope effects, and the exclusive cis-selectivity of cyclization, a mechanism involving a C-H activation motif has been proposed for this transformation. Copyright
