☆ 4.6 Review

Photo-induced radical transformations of tosyl cyanide

ORGANIC & BIOMOLECULAR CHEMISTRY (2023)

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Jing-Feng Zhao et al.

Summary: A one-step protocol for desulfonylative allylation of C-H bonds using TBADT as a photo-hydrogen atom transfer catalyst is demonstrated. This method shows good functional group tolerance and can be applied for allylation of aldehydes and alkanes.

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Peng-Zi Wang et al.

Summary: Creating, conserving, and modifying the stereochemistry of organic compounds is an important area of research in synthetic chemistry. Stereochemical editing, as an alternative strategy, allows for late-stage alteration of stereochemistry, but it often faces thermodynamic barriers. Photocatalysis, by using photogenerated radical species, can overcome these barriers and enable contra-thermodynamic stereochemical editing processes.

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Summary: The electrochemical alkene difunctionalization reaction is an efficient and sustainable method for constructing vicinal difunctionalized structures in organic synthesis. It eliminates the need for additional redox catalysts, metal catalysts, or chemical oxidants and avoids the generation of chemical waste by solely using electrons as the redox agents. This review summarizes the recent advancements in electrochemical alkene difunctionalization, focusing on reaction features, scope, limitations, and mechanistic rationalizations of three categories of alkene difunctionalization methods: nucleophile-terminated, radical-terminated, and functionality migration-terminated reactions.

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Article Chemistry, Multidisciplinary

Water-mediated radical C-H tosylation of alkenes with tosyl cyanide

Dongyan Hu et al.

Summary: The water-mediated tosylation of alkenes with tosyl cyanide was studied, revealing the formation of sulfinyl sulfone as the catalyst in the presence of water. The sulfinyl sulfone species decomposed into a sulfonyl radical and a sulfinyl radical through homolytic fission. The vinyl sulfone was obtained through sequential addition of the alkene to the sulfonyl radical and the sulfinyl radical, followed by beta-elimination of a sulfinyl moiety.

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Kai Sun et al.

Summary: An efficient photochemical radical sulfonyl cyclization method was developed for the synthesis of medium-sized benzo[b]azocines and benzo[b] azonines. This chemoselective method allows the synthesis of highly functionalized eight- and nine-membered N-heterocycles. Experimental studies and computational calculations were used to understand the radical mechanism and rationalize the observed chemoselectivity. The large-scale synthesis and derivatizations demonstrated the potential utility of this strategy for the synthesis of valuable medium-sized N-heterocycles.

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Wei Lin et al.

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Jian-Jun Dai et al.

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Chunhua Ma et al.

Summary: A comprehensive study on a transition-metal-free visible-light-promoted 3-acetalation reaction of quinoxaline-2(1H)-ones is presented. The reaction successfully constructs various acetalated quinoxaline-2(1H)-ones in moderate to good yields using an inexpensive photocatalyst and a radical source. The method demonstrates versatility in late-stage modification of drug molecules and various functionality transformations.

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Shu-Lin Meng et al.

Summary: The Odyssey of photochemistry involves manipulating electrons and protons in time, space, and energy. While single-electron photochemical transformations have achieved remarkable success, achieving multielectron and proton reactions is exponentially challenging. Optimizing light harvesting, accelerating consecutive electron transfer, manipulating catalyst-substrate interactions, and coordinating proton transfer kinetics are necessary to achieve selective bond formations. Tandem catalysis enables coordination between different photochemical events and catalytic transformations, facilitating multielectron redox chemistries and consecutive, value-added reactivities. Collaborative efforts in molecular and material design, mechanistic understanding, and theoretical modeling will unlock opportunities for multielectron and proton transformations with enhanced versatility, efficiency, selectivity, and scalability, ultimately leading to a more sustainable society.

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY (2022)

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Visible-Light-Mediated C3-H Acetalation of Quinoxalin-2(1H)-ones

Zhang Mengqi et al.

Summary: Visible-light-mediated catalytic decarboxylic acetalation of quinoxalin-2(1H)-ones with glyoxylic acid acetalde using 1,2,3,5-tetrakis(carbazol-9-yl)-4,6-dicyanobenzene (4CzIPN) has been reported. The reaction provides a green and efficient approach to construct a series of 3-acetal quinoxalin-2(1H)-ones using air as the oxidant at room temperature. The reaction involves a visible-light promoted radical reaction process.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2022)

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Photocatalyzed Oxidative Cross-Coupling Reaction to Access Symmetrical/Unsymmetrical Thiosulfonates

Zhao Jianming et al.

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CHINESE JOURNAL OF ORGANIC CHEMISTRY (2022)

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Visible Light-Induced 4-Chromanones Synthesis: Radical Cascade Cyclization of α-Oxocarboxylic Acids with o-(Allyloxy)arylaldehydes Promoted by Phenyliodine(III) Diacetate

Xuyu Zhou et al.

Summary: An efficient and sustainable method for the synthesis of 1,4-diketone containing chromanone derivatives has been developed using visible light-promoted cascade radical cyclization. The reaction occurs under mild conditions, such as room temperature and blue LED irradiation, without the need for a photoredox catalyst, and provides moderate to good yields of the final heterocycles.

CHINESE JOURNAL OF ORGANIC CHEMISTRY (2022)

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Switchable aroylation and diaroylation of allyl sulfones with aldehydes enabled by decatungstate photocatalysis

Lipeng Qiao et al.

Summary: A photocatalytic strategy using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer (HAT) photocatalyst and aldehydes as radical precursors was developed for the controllable aroylation or diaroylation of allyl sulfones. By adjusting the substrate ratio, the selectivity of the reaction could be easily tuned, resulting in the installation of various aroyl groups on allyl sulfones, and the formation of beta,gamma-unsaturated ketones and 1,5-diketones with moderate to excellent yields. This methodology offers mild conditions, high step economy, no external additive, readily available resources, and broad substrate scope.

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CHINESE JOURNAL OF ORGANIC CHEMISTRY (2022)

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Decatungstate-photocatalyzed direct coupling of inert alkanes and quinoxalin-2(1H)-ones with H2 evolution

Xiao-Ya Yuan et al.

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Direct C(sp3)-H Cyanation Enabled by a Highly Active Decatungstate Photocatalyst

Kunsoon Kim et al.

Summary: A highly efficient, direct C(sp(3))-H cyanation method was developed under mild photocatalytic conditions, allowing for the direct cyanation of various C(sp(3))-H substrates with excellent functional group tolerance. Complex natural products and bioactive compounds can be efficiently cyanated using this method.

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