Aug 2026· ACS Omega· Vol 11, pp. 53258 - 53264· 0 citations· 48 references
Medicine
Abstract
C–S bond formation via hydrogen atom transfer (HAT) remains underdeveloped despite the importance of thioethers in organic synthesis, materials science, and medicinal chemistry. Herein, we report a mild, rapid, and operationally simple method for the direct α-C(sp3)–S bond formation in ethers using alkyl or aryl thiosulfonates as sulfur sources and (4-methoxyphenyl)(4-(trifluoromethyl)phenyl)methanone as the diaryl ketone catalyst. The reaction proceeds at room temperature under a 390 nm irradiation, delivering a broad range of thioethers in the absence of metals or stoichiometric oxidants. The method exhibits excellent functional group tolerance, predictable regioselectivity favoring the most hydridic C–H bonds, and compatibility with various cyclic and acyclic ethers and amides. Preliminary mechanistic studies support a radical pathway consistent with a well-established photoexcited ketone-mediated HAT followed by radical addition to the thiosulfonate. This approach expands the toolkit for redox-neutral C(sp3)–S bond construction.
Non-canonical amino acids (ncAAs) are key privileged structural motifs in drug discovery. However, their synthesis via C–H functionalization is often hampered by poor functional group tolerance and narrow substrate scope, and largely restricted to activated ethereal or benzylic C–H bonds. Herein, we report a green ph...
Si-Yu Hu, Hao-Ran Chen, Sheng Zhou et al.· Journal of Organic Chemistry· 0 citations
The selective α-C(sp3)-H functionalization of amines has emerged as a valuable strategy for the rapid construction of structurally diverse and synthetically important amine architectures. Among the various approaches developed for α-amino radical generation, intramolecular radical translocation via hydrogen atom transf...
Vinjamuri Srinivasu, Kanak Ranjan Saha, Shalini Bagchi et al.· Chemical Communications· 0 citations
Here, we report an iron-catalyzed aerobic transformation that activates N/O/S-α-C(sp3)–H bonds under blue light irradiation, forming hemiacetal-type analogues, amenable for trapping with diverse commercially available N-, O-, S-, and C-nucleophiles. The method achieves azolation, amination, acetalization, hydroxylation...
Xin-Long Zhou, Jia-Yin Li, Nan Huang et al.· Chemical Science· 0 citations
The direct conversion of vinyl halides into oxygenated sulfur-containing carbonyl compounds using water as the oxygen source remains challenging because it requires coordinated C-halogen activation, radical capture, oxygen incorporation, and C–S bond formation under mild conditions. Here we report a photoinduced electr...
I. Karmakar, Ling-You Chang, Ci-Yang Sun et al.· Organic Letters· 0 citations
Tuning the reactivity of highly active radical intermediates is a serious challenge in organic synthesis. Herein, we describe an unexpected protocol involving visible-light-driven ligand-to-metal charge-transfer (LMCT) excited states of copper(II) chlorides and diether complexes to achieve chemoselectivity between dist...
Zhong-Shan Teng, Xin-Yu Zhang, Yu-Rong Yang et al.· Journal of Organic Chemistry· 0 citations
The catalytic synthesis of both (E)- and (Z)-haloalkenes from internal aryl alkyl alkynes via a sulfur-boron Lewis pair has been developed. The catalytically active Lewis pair complex is generated in situ from 2-naphthalenethiol and B(C6F5)3, enabling the selective synthesis of chloro-, bromo-, and iodoalkenes with exc...
Yunsoo Shim, Jin Qian, Sourav Dey et al.· Angewandte Chemie· 0 citations
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