Science Faculty

Methyl Sulfinates as Electrophiles in Friedel-Crafts Reactions. Synthesis of Aryl Sulfoxides

Author/s

Yuste, F.; Hernández Linares, A.; Mastranzo, V. M.; Ortiz, B.; Sánchez-Obregón, R.; Fraile, A.; García Ruano, J. L.

Año de edición

2011

Referencia completa

J. Org. Chem. 2011, 76, 4635-4644. DOI: 10.1021/jo2006335

Resumen

The Friedel
Crafts reaction of methyl alkyl- and arylsulfinates with aromatic systems, activated by one or more electron-donating substituents (OH, OMe, NHR, NR2), provides
alkyl aryl and diaryl sulfoxides under mild conditions and in moderate to good yields. The very high regioselectivity usually observed in these sulfinylation reactions is rationalized
on the basis of a Wheland intermediate having a trigonal bypyramidal structure in which steric and electronic interactions are significant factors strongly destabilizing the attack to the ortho positions.