Acetalization Allows the Photoheterolysis of the Ar-Cl Bond in Chlorobenzaldehydes and Chloroacetophenones

作者:Raviola Carlotta; Protti Stefano; Ravelli Davide; Mella Mariella; Albini Angelo; Fagnoni Maurizio*
来源:Journal of Organic Chemistry, 2012, 77(20): 9094-9101.
DOI:10.1021/jo3016264

摘要

The nonaccessibility of phenyl cations by irradiation of electron poor aryl chlorides was circumvented by transforming the carbonyl group of aromatic ketones or aldehydes into the corresponding 1,3-dioxolanes and the carboxyl group of benzoate ester into an orthoester functionality. This transformation allowed the heterolytic photoactivation of the Ar-Cl bond in protic media and the generation of phenyl cations. In the presence of pi-bond nucleophiles, arylated products were obtained in good to excellent yields.

  • 出版日期2012-10-19