Sep 2026· Chemical Science· 0 citations· 2 references
Medicine
Abstract
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, thiolation, alkylation, and arylations across ethers, thioethers and pyrrolidines with high chemoselectivity and regioselectivity. Mechanistic studies indicate that this system synergizes iron-catalyzed photoinduced LMCT, followed by chlorine radical-initiated HAT and subsequent O2 trapping of the resulting alkyl radicals to afford key hemiacetal-type intermediates. Significantly, FeCl3 serves a triple catalytic role by generating chlorine radicals, functioning as a redox shuttle and acting as a Lewis acid activator.
Palladium(II) complexes of the TPA family (TPA = tris(2-pyridylmethyl)amine) catalyze selective C(sp3)-H oxyfunctionalizations but have so far been unable to activate "green" oxidant H2O2, instead requiring peroxycarboxylic acids (2-4 equiv, best results coming with m-CPBA). Herein, we show that hydrogen peroxide itsel...
D. P. Lubov, Elizaveta M. Zhernikova, K. Bryliakov· Organic Letters· 0 citations
The use of ester-derived electrophiles in transition-metal-free electroreductive C(sp3)─C(sp3) bond formation remains largely unexplored. Herein, we report a sacrificial-anode-enabled electroreductive cross-coupling of simple unsaturated carboxylates with unactivated alkyl halides. Aryl, alkenyl, and alkynyl carboxylat...
The development of an environmentally benign protocol for the site-selective γ-C(sp3)-H acylation of aliphatic amines is of significant interest given their utility in accessing a diverse collection of γ-aminoketones prevalent in biologically active compounds. Herein, we report a visible-light-driven γ-C(sp3)-H acylati...
Ramesh Gorre, Qing-Yun Zhi, Xuan Huang et al.· Organic Letters· 0 citations
Radical-mediated transition-metal-catalyzed C─H carbonylation represents a direct and powerful approach for the synthesis of carbonyl compounds; however, the stoichiometric oxidants typically required for hydrogen atom abstraction hamper the extensive application of these protocols and raise environmental concerns. In...
Cheng-Cheng Fan, Jia-Ning Wu, Peng Wang et al.· Angewandte Chemie· 0 citations
The visible-light-driven photocatalytic decarboxylation of α-aryloxy carboxylic acids produces α-oxy carbon-centered radicals that undergo intramolecular Giese addition to form 2,3-dihydrobenzofurans, chromans, 2,3,4,5-tetrahydrobenzo[b]oxepines, and 3,4,5,6-tetrahydro-2H-benzo[b]oxocines. In contrast to the existing m...
Igor Topalović, Markus Lange, I. Vilotijević· Journal of Organic Chemistry· 0 citations
Herein, we report an electron donor-acceptor (EDA) complex-driven strategy for the three-component cascade annulation of 2-vinyloxydiphenylacetylene, thiols, and 4-cyanopyridine, enabling the regioselective synthesis of C-2 α-thiomethylated and C-3 pyridylmethylated benzofuran derivatives. This protocol features high e...
Chuang Liu, Tong Hu, Tian-Tian Xu et al.· Chemical Communications· 0 citations
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