Work

Photoactivation of Electron Donor–Acceptor Complexes Enables Deoxygenative Hydrogenation and Deuteration

Year: 2026

Type: article

Abstract: ABSTRACT In recent years, reactions driven by photoactivated electron donor–acceptor (EDA) complexes have attracted significant attention from the synthetic community. Herein, we report a photoinduced deoxygenative hydrogenation via photoactivation of EDA complexes, employing a cost‐effective and readily available NHC‐borane reagent with common PhO‐substituted thiocarbonates—or even MeS‐substituted xanthates—as substrates. This method, however, was not applicable to acyclic tertiary alcohol‐derived xanthates because of their high propensity for competitive Chugaev elimination. To address this limitation, an alternative photocatalytic deoxygenation approach using oxalate esters was developed for this substrate class. Furthermore, to explore the potential of NHC‐boranes in deuteration reactions, we established a novel photoinduced protocol for synthesizing NHC‐BD 3 using D 2 O as the deuterium source, circumventing the need for expensive NaBD 4 . This approach afforded six distinct NHC‐BD 3 compounds in good yields with high levels of deuterium incorporation. The newly synthesized NHC‐BD 3 demonstrated broad utility in both photoinduced deoxygenative deuteration and reductive deuteration of ketones and aldehydes.

Source: Transformative Chemistry

DOI: 10.1002/tch2.70019

Authors: Mengqing Zhang, Changlei Zhu, Jingjing Wu

Institutions: Shanghai Jiao Tong University, Suqian University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid