Visible-light-promoted EDA complex enables cascade annulation of 2-vinyloxydiphenylacetylene with thiols and 4-cyanopyridine: facile access to diverse 2,3-difunctionalized benzofurans.
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 efficiency, no requirement for an external photocatalyst, broad substrate scope with good functional group compatibility and mild reaction conditions. Mechanistic studies indicate a radical pathway featuring regiospecific addition, annulation, and cross-coupling of the in situ-formed radical intermediate, while sequential protonation and deprotonation ultimately drive aromatization.
Cyclohepta[b]indoles are important nitrogen-containing heterocycles, yet their efficient synthesis remains challenging. Herein, we report a visible-light-promoted formal [4 + 3] cyclization of 3-difluorobromoacetylindoles with vinyldiazos through a photoredox cascade radical process. This method provides straightforwar...
A visible-light-mediated three-component radical cascade cyclization of 2-(methylthio)phenyl isocyanides, terminal alkynes, and arylsulfonyl chlorides is reported, enabling modular and regioselective synthesis of C2 alkenylsulfonyl-substituted benzothiazoles. This photoredox strategy allows one-pot construction of conj...
Yang Li, Shi-Chao Yang, Cheng Jiang et al.· Journal of Organic Chemistry· 0 citations
This study develops a visible-light-induced electron donor-acceptor (EDA) complex strategy, employing the inexpensive and readily available DBU as the electron donor and the industrially available CF3Br as the trifluoromethyl source, to achieve the trifluoromethylation/heteroarylation of alkenes. This method offers adv...
Zhi-Jun Zhu, Xiaopeng Hai, Yu-Yu Lv et al.· Journal of Organic Chemistry· 0 citations
Imidazo[1,2-a]pyridines are privileged heterocyclic motifs in pharmaceuticals and functional materials, yet densely substituted azaarenyl-containing variants remain difficult to access. We report a visible-light-driven, Brønsted acid-catalyzed annulation of readily accessible N-(2-azaarenyl)enaminones. The reaction pro...
Given their biological and synthetic importance, the construction of 9,10-dihydronaphthalene scaffolds is a pivotal transformation in organic synthesis, serving as a gateway to various bioactive natural products and functional materials. Herein, we develop a visible-light-driven, EDA-mediated Heck-type arylation/[4+2]...
Jing-Ying Liu, Ke-Yi Deng, Kai Chen et al.· Organic Letters· 0 citations
An efficient nickel-catalyzed thiolative addition-cyclization of conjugated cyclic enynones for the synthesis of 9-sulfenyl-2,3-dihydrophenanthren-4-(1H)-ones is described. The reaction proceeds through a nickel-catalyzed hydrothiolation of cyclic enynones, followed by visible-light-induced intramolecular cyclization....
Arundhati Sahu, Kanagaraj Madasamy, B. Baskar et al.· ACS Omega· 0 citations
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