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Electronic and steric effects in the rhodium-complex catalysed co-cyclization of alkynes and nitriles to pyridine derivatives

1993; Elsevier BV; Volume: 447; Issue: 2 Linguagem: Inglês

10.1016/0022-328x(93)80252-7

1872-8561

Pietro Diversi, Luca Ermini, Giovanni Ingrosso, Antonio Lucherini,

Catalytic Alkyne Reactions

A study of the properties exhibited by the catalyst precursors of formula [Rh(η5-C5H4R)(C2H4)2] (R  NMe2, tBu, Me, H, Cl, NO2, CF3, or COOMe) in the co-cyclization of a variety of 1-alkynes (R′CCH) and nitriles (R″CN) to pyridine derivatives is reported. Initial reaction rates as well as chemoselectivity and regioselectivity are markedly influenced by the electron donor—acceptor properties of the R groups on the cyclopentadienyl ring, as well as by the steric and electronic effects induced by the substituents (R′ and R″) attached to substrates.