The cyclization of N-allyl-N-carbetoxy-substituted aminothiophenes and furans was performed by intramolecular Pd(II)- catalyzed oxidative coupling. The process involves a nucleophilic attack of a heteroaromatic carbon to the internal carbon of the π-olefin complex through a 5-exo-trig ring-formation. Better conditions required PdCl2(MeCN)2 as catalyst, CuCl2 as co-catalyst and an environmentally friendly reoxidant such as O2 to promote the catalytic cycle.
Intramolecular palladium-catalyzed oxidative coupling on thiophene and furan rings : Determinant role of the electronic availability of the heterocycle / E. Beccalli, E. Borsini, G. Broggini, M. Rigamonti, S. Sottocornola. - In: SYNLETT. - ISSN 0936-5214. - 2008:7(2008), pp. 1053-1057.
Intramolecular palladium-catalyzed oxidative coupling on thiophene and furan rings : Determinant role of the electronic availability of the heterocycle
E. BeccalliPrimo
;
2008
Abstract
The cyclization of N-allyl-N-carbetoxy-substituted aminothiophenes and furans was performed by intramolecular Pd(II)- catalyzed oxidative coupling. The process involves a nucleophilic attack of a heteroaromatic carbon to the internal carbon of the π-olefin complex through a 5-exo-trig ring-formation. Better conditions required PdCl2(MeCN)2 as catalyst, CuCl2 as co-catalyst and an environmentally friendly reoxidant such as O2 to promote the catalytic cycle.Pubblicazioni consigliate
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