1-Methylpyridine-2(1H)-thione Photocatalyzed Giese Reaction with N-Hydroxyphthalimide Esters via Single Electron Transfer
Lanting Li , Yuzhuo Wang , Li Yuan , Xinjun Tang
Chinese Journal of Chemistry ›› 2025, Vol. 43 ›› Issue (8) : 911 -915.
1-Methylpyridine-2(1H)-thione Photocatalyzed Giese Reaction with N-Hydroxyphthalimide Esters via Single Electron Transfer
We have developed a series of 1-methylpyridine-2(1H)-thione (MPT) analogues to be used as organocatalysts. The MPT catalysts are easily prepared and bench-stable. In our previous work, we found that the ground-state MPT catalyst could act as a nucleophile to generate primary radicals via an SN2 pathway. However, this reaction was limited to benzyl radicals. Herein, we reported a new catalytic property of the MPT catalyst. The photoexcited MPT catalyst (E(MPT·+/MPT*) = –1.60 V vs. Ag/AgCl in MeCN) could reduce NHPI esters through a single electron transfer process. Various carbon radicals, including benzyl radical, as well as primary, secondary and tertiary alkyl radicals, could be generated easily. Notably, amino acids, peptide, pharmaceuticals, and other biologically active molecules could be modified by using this methodology showing the potential synthetic utility of this method.
MPT catalyst / NHPI esters / Giese reaction / Photocatalyst / Amino acids / Catalytic activity / Radical reactions / Homogeneous catalysis
2025 SIOC, CAS, Shanghai, & WILEY-VCH GmbH
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