Electrifying P(V): Access to Polar and Radical Reactivity

Mahdi Jafarzadeh; Molhm Nassir; Luca Gherardi; Nicholas Raheja; Yu Kawamata; Phil S Baran

doi:10.1002/anie.202421163

Electrifying P(V): Access to Polar and Radical Reactivity

Angew Chem Int Ed Engl. 2025 Jan 6:e202421163. doi: 10.1002/anie.202421163. Online ahead of print.

Authors

Mahdi Jafarzadeh¹, Molhm Nassir¹, Luca Gherardi², Nicholas Raheja¹, Yu Kawamata¹, Phil S Baran³

Affiliations

¹ The Scripps Research Institute, chemistry, UNITED STATES OF AMERICA.
² University of Pisa Department of Chemistry and Industrial Chemistry: Universita degli Studi di Pisa Dipartimento di Chimica e Chimica Industriale, chemistry, ITALY.
³ The Scripps Research Institute, Department of Chemistry, 10550 North Torrey pines Road, BCC-169, 92037, La Jolla, UNITED STATES OF AMERICA.

PMID: 39761190
DOI: 10.1002/anie.202421163

Abstract

Electrochemical, fully stereoselective P(V)-radical hydrophosphorylation of olefins and carbonyl compounds using a P(V) reagent is disclosed. By strategically selecting the anode material, radical reactivity is accessible for alkene hydrophosphorylation whereas a polar pathway operates for ketone hydrophosphorylation. The mechanistic intricacies of these chemoselective transformations were explored in-depth.

Keywords: Electrochemistry* Radical Reaction* Abramov* P(V); PSI; Thiophosphate.