Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation

Yohei Ogiwara; Yuka Sakurai; Hiroyuki Hattori; Norio Sakai

doi:10.1021/acs.orglett.8b01582

Palladium-Catalyzed Reductive Conversion of Acyl Fluorides via Ligand-Controlled Decarbonylation

Org Lett. 2018 Jul 20;20(14):4204-4208. doi: 10.1021/acs.orglett.8b01582. Epub 2018 Jul 2.

Authors

Yohei Ogiwara¹, Yuka Sakurai¹, Hiroyuki Hattori¹, Norio Sakai¹

Affiliation

¹ Department of Pure and Applied Chemistry, Faculty of Science and Technology , Tokyo University of Science , Noda , Chiba 278-8510 , Japan.

PMID: 29963866
DOI: 10.1021/acs.orglett.8b01582

Abstract

Ligand-controlled non-decarbonylative and decarbonylative conversions of acyl fluorides were developed using a Pd(OAc)₂/Et₃SiH combination. When tricyclohexylphosphine (PCy₃) was used as the ligand, aldehydes were obtained as simple reductive conversion products. The use of 1,2-bis(dicyclohexylphosphino)ethane (Cy₂P(CH₂)₂PCy₂, DCPE) as the ligand, however, favored the formation of hydrocarbons, which are decarbonylative reduction products.

Publication types

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