Work

Enhanced Efficiency of Amide‐Substituted Quinuclidine‐Boranes as Hydridic Hydrogen Atom Transfer Catalysts for Photoinduced Hydroalkylation of Unactivated Olefins†

Year: 2024

Type: article

Abstract: Comprehensive Summary An amide‐substituted quinuclidine‐borane has been identified as a more efficient hydridic hydrogen atom transfer (HAT) catalyst for the hydroalkylation of unactivated olefins under visible‐light irradiation. 1H NMR titration experiments reveal that the amide moiety of the quinuclidine‐borane catalyst forms stronger hydrogen bonds with the carbonyl substrates, thereby improving the reaction yields. Furthermore, it was found that the reaction yields correlate well with the association constant between the quinuclidine‐borane catalyst and the carbonyl substrate. A scale‐up reaction using a continuous‐flow photoreactor has also been demonstrated.

Source: Chinese Journal of Chemistry

DOI: 10.1002/cjoc.202400725

Authors: Xiao Yang, Mengdi Ma, Meichen Xu, Yubing Pang, Haiying Zhao, Juntao Ye

Institutions: Shanghai Jiao Tong University, Inner Mongolia University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: bronze

Funders: National Natural Science Foundation of China, Shanghai Jiao Tong University

Awards: G145556382, G2589481472, G349242031