Metal-catalyzed cross-electrophile couplings have become a valuable tool for carbon-carbon bond formation. This minireview provides a comprehensive overview of the recent developments in the topical field of cross-electrophile couplings, provides explanations of the current state-of-the-art, and highlights new opportunities arising in the emerging fields of photoredox catalysis and electrochemistry.

The N-heterocyclic carbene-catalyzed oxidative [3 + 2] annulation of dioxindole and enals was developed, giving the corresponding spirocyclic oxindole-γ-lactones in good yields with high to excellent diastereo- and enantioselectivities.

Olefins are prevalent substrates and functionalities. The synthesis of olefins from readily available starting materials such as alcohols, amines and carboxylic acids is of great significance to address the sustainability...

Herein, we report an enantioselective synthesis of azepinones via the N-heterocyclic carbene (NHC) catalyzed [3+4] annulation reaction of isatin-derived enals and aurone-derived azadienes. The corresponding spirocyclic oxindolebenzofuroazepinones were obtained in good yields, with excellent diastereo-and enantioselectivities. The resulted azepinones were evaluated for their in vitro cytotoxic activities against six human tumor cell lines, with two compounds showing significant inhibitory activity comparable with that of cisplatin.

The oxidative N-heterocyclic carbene-catalyzed [3 + 2] annulation of β,β-disubstituted enals and dioxindoles was developed, giving the spirocyclic oxindole-γ-lactones bearing two contiguous tetrasubstituted stereocenters in good yields with excellent diastereoselectivities and good enantioselectivities.

While N-hydroxyphthalimide (NHPI) ester has emerged as a powerful reagent as an alkyl radical source for a variety of C–C bond formations, the corresponding C­(sp3)–N bond formation is still in its infancy. We demonstrate herein transition-metal-free decarboxylative C­(sp3)–X bond formation enabled by the photochemical activity of the NHPI ester–NaI–NHC complex, giving primary C­(sp3)–(N)­phth, secondary C­(sp3)–I, or tertiary C­(sp3)–(meta C)­phth coupling products. The primary C­(sp3)–(N)­phth coupling offers convenient access to primary amines.

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TheN -heterocyclic carbene-catalyzed [3+ +3] annulation of indoline-2-thiones and bromoenals hasb een developed, giving the corresponding indolo[2,3-b]dihydrothiopyranones in high yields.