Work

Development of a General Organophosphorus Radical Trap: Deoxyphosphonylation of Alcohols

Year: 2024

Type: article

Abstract: Here we report the design of a general, redox-switchable organophosphorus alkyl radical trap that enables the synthesis of a broad range of C( sp 3 )–P(V) modalities. This “plug-and-play” approach relies upon in situ activation of alcohols and O═P(R 2 )H motifs, two broadly available and inexpensive sources of molecular complexity. The mild, photocatalytic deoxygenative strategy described herein allows for the direct conversion of sugars, nucleosides, and complex pharmaceutical architectures to their organophosphorus analogs. This includes the facile incorporation of medicinally relevant phosphonate ester prodrugs.

Source: Journal of the American Chemical Society

DOI: 10.1021/jacs.4c00557

Authors: Noah B. Bissonnette, Niels Bisballe, Andrew V. Tran, James A. Rossi-Ashton, David W. C. MacMillan

Institution: Princeton University

Language: English

Topic: Organophosphorus compounds synthesis

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze