In recent years, visible light-driven organic photochemical synthesis has attracted wide research interest from academic and industrial communities due to its features of green and sustainable chemistry. In this flourishing area, Chinese chemists have devoted great efforts to different aspects of synthetic chemistry. This review will summarize their representative work according to the following categories: C–H functionalization, synthesis of aromatic aza-heterocycles, asymmetric organic photochemical synthesis, transformations of small molecules and biomolecule-compatible reactions.

Visible light-driven organic photochemical synthesis in China

Fil: Yerien, Damian Emilio. Consejo Nacional de Investigaciones Cientificas y Tecnicas; Argentina. Universidad de Buenos Aires. Facultad de Farmacia y Bioquimica. Departamento de Quimica Organica; Argentina

Difluoromethylation Reactions of Organic Compounds.

Rearrangement reactions, one of the most significant transformations in organic chemistry, play an irreplaceable role in improving synthetic efficiency and molecular complexity. Concomitant cleavage and reconstruction of chemical bonds can display the great artistry and the glamour of synthetic chemistry. Over the past century, ionic rearrangement reactions, in particular those involving cationic pathways, have represented most of the research. Alongside the renaissance of radical chemistry, radical-mediated rearrangements have recently seen a rapid increase of attention from the chemical community. Many new radical rearrangements that extensively reveal the migratory behaviour of functional groups have been unveiled in the last decade. This Review provides a comprehensive perspective on the area from the past to present achievements, and brings up the prospects that may inspire colleagues to develop more useful synthetic tools based on radical rearrangements.

Radical-mediated rearrangements: past, present, and future.

The selective incorporation of fluorinated motifs, in particular CF2FG (FG=a functional group) and CF2H groups, into organic compounds has attrracted increasing attention since organofluorine molecules are of the utmost importance in the areas of nuclear imaging, pharmaceutical, agrochemical, and material sciences. A variety of synthetic approaches has been employed in late‐stage difluoroalkylation reactions. Visible light photoredox catalysis for the production of CF2FG and CF2H radicals has provided a more sustainable alternative to other conventional radical‐triggered reactions from the viewpoint of safety, cost, availability, and “green” chemistry. A wide range of difluoroalkylating reagents has been successfully implemented in these organic transformations in the presence of transition metal complexes or organic photocatalysts. In most cases, upon excitation via visible light irradiation with fluorescent light bulbs or blue light‐emitting diode (LED) lamps, these photocatalysts can act as both reductive and oxidative quenchers, thus enabling the application of electron‐donor or electron‐acceptor difluoroalkylating reagents for the generation of CF2FG and CF2H radicals. Subsequent radical addition to substrates and additional organic transformations afford the corresponding difluoroalkylated derivatives. The present review describes the distinct strategies for the transition metal‐ and organic‐photocatalyzed difluoroalkylation of a broad range of organic substrates by visible light irradiation reported in the literature since 2014.






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Progress in Difluoroalkylation of Organic Substrates by Visible Light Photoredox Catalysis

As the "chemical chameleon", sulfonyl-containing compounds and their variants have been merged with various types of reactions for the efficient construction of diverse molecular architectures by taking advantage of their incredible reactive flexibility. Currently, their involvement in radical transformations, in which the sulfonyl group typically acts as a leaving group via selective C-S, N-S, O-S, S-S, and Se-S bond cleavage/functionalization, has facilitated new bond formation strategies which are complementary to classical two-electron cross-couplings via organometallic or ionic intermediates. Considering the great influence and synthetic potential of these novel avenues, we summarize recent advances in this rapidly expanding area by discussing the reaction designs, substrate scopes, mechanistic studies, and their limitations, outlining the state-of-the-art processes involved in radical-mediated desulfonylation and related transformations. With a specific emphasis on their synthetic applications, we believe this review will be useful for medicinal and synthetic organic chemists who are interested in radical chemistry and radical-mediated desulfonylation in particular.

Desulfonylation via Radical Process: Recent Developments in Organic Synthesis.

We reported a visible-light-induced difluoroalkylation and cyclization cascade reaction of 1,8-enynes with broad substrate scopes in up to 92% isolated yields. This method provides a sustainable and efficient access to the synthesis of difluoroalkylated tetracyclic compounds under mild conditions.

Sustainable Difluoroalkylation Cyclization Cascades of 1,8-Enynes

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Sustainable Difluoroalkylation Cyclization Cascades of 1,8-Enynes