Work

Mild Hydroalkylation of Terminal Olefins Via Decatungstate/Thiol Cooperative Photocatalysis

Year: 2025

Type: article

Abstract: Here we report the use of a tetrabutylammonium decatungstate (TBADT)/thiol photocatalytic system for selective addition of acetone and other simple ketone, nitrile, and chlorocarbon functionalities to terminal olefins. This system avoids the use of energetic reagents such as peroxides and proceeds under mild conditions using Earth-abundant element catalysts, providing a sustainable approach to C-C bond formation using activated olefins. Initial exploration reveals that hydroalkylation of unactivated olefins is also possible, though in lower efficiency, and preliminary mechanistic experiments are consistent with a radical mechanism.

Source: Organic Letters

DOI: 10.1021/acs.orglett.5c01088

Authors: Austin J. Moser, Paige E. Sutter, Alex M. Chavez, Sebastian A. Cruz, Julian G. West

Institution: Rice University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: Welch Foundation, Cancer Prevention and Research Institute of Texas, National Institute of General Medical Sciences, Division of Chemistry

Awards: G1510748105, Recruitment of First-Time, Tenure-Track Faculty Members, G2358703021, G2474473178