Details

Autor(en) / Beteiligte

• Curto, John M
• Kozlowski, Marisa C

Titel

Chemoselective activation of sp(3) vs sp(2) C-H bonds with Pd(II)

Ist Teil von

• Journal of the American Chemical Society, 2015-01, Vol.137 (1), p.18-21

Ort / Verlag

United States

Erscheinungsjahr

2015

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• The first selective coupling of a carbon nucleophile with methyl, ethyl, propyl, and butyl arenes in the absence of a directing group is described. Pd(OAc)2 double C-H activation displays remarkable selectivity for the terminal methyl sites in alkyl arenes, rather than the more commonly observed arene sp(2) C-H activation. Mechanistic studies indicate the intermediacy of an azlactone dimer, obtained from oxidation with Pd(OAc)2, and are consistent with a Pd-catalyzed C-H activation vs a radical process. The observed reactivity establishes that typical reaction solvents (e.g., toluene) can readily participate in C-H activation chemistry.