Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates

Masaaki Komatsuda; Kei Muto; Junichiro Yamaguchi

doi:10.1021/acs.orglett.8b01807

Pd-Catalyzed Dearomative Allylation of Benzyl Phosphates

Org Lett. 2018 Jul 20;20(14):4354-4357. doi: 10.1021/acs.orglett.8b01807. Epub 2018 Jul 5.

Authors

Masaaki Komatsuda¹, Kei Muto¹, Junichiro Yamaguchi¹

Affiliation

¹ Department of Applied Chemistry , Waseda University , 3-4-1 Ohkubo , Shinjuku, Tokyo 169-8555 , Japan.

PMID: 29975060
DOI: 10.1021/acs.orglett.8b01807

Abstract

Dearomative C-C bond formation of benzyl phosphates has been developed. In the presence of a palladium/PAr₃ catalyst, benzyl phosphates reacted with allyl borates to generate the allylated product in a dearomative fashion. The resulting dearomatized molecules were successfully derivatized by Simmons-Smith cyclopropanation and oxidation.

Publication types

Research Support, Non-U.S. Gov't