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Research Progress in Synthesis and Application of Thiosulfonates

Oxidative Dehydrogenative Coupling of Thiols with Alkanes for the Synthesis of Sulfoxides.

We, herein, describe a copper-mediated domino CuAAC intramolecular selanylation for the synthesis of unprecedented fused benzo[4,5][1,3]selenazolo[3,2-c][1,2,3]triazoles from 1,2-bis(2-azidoaryl)diselenides and terminal alkynes under microwave irradiation. This is the seminal method for the synthesis of these fused heterocycles, and it proceeds under mild conditions, tolerates several functional groups, and can be carried out using environmentally benign solvents such as dimethyl carbonate. This transformation has been successfully extended to TMS-protected alkynes and to bioactive alkynes. A plausible reaction mechanism is proposed based on several control experiments and previous reports.

Copper-Mediated Intramolecular Interrupted CuAAC Selanylation.

A copper-catalyzed cascade multicomponent reaction for synthesizing ditriazolyl diselenides from azides, terminal alkynes, and elemental selenium has been developed. The present reaction features utilizing readily available and stable reagents, high atom-economy, and mild reaction conditions. A possible mechanism is proposed.

Copper-Catalyzed Cascade Multicomponent Reaction of Azides, Alkynes, and Selenium: Synthesis of Ditriazolyl Diselenides.

2-Pyrazolines are important five-membered heterocycles, containing two adjacent nitrogen atoms. They can incorporate various functional groups and possess unique biological properties. Moreover, they have been used as useful building blocks. In recent years, the field of 2-pyrazoline synthesis has experienced enormous progress. Novel strategies have been developed, and many studies reporting improvements or adaptations of existing protocols have been published, giving access to new functionalizations, unexplored structures, and/or enantioselective synthesis. This review summarizes the progress made in synthetic methodologies during the period from 2012 to 2022. The functionalization challenges and capabilities, scopes and limitations of the reactions, substitution patterns, and mechanisms of the reactions, where appropriate, will be discussed. 

Strategies and Methods for the Synthesis of 2‐Pyrazolines: Recent Developments (2012‐2022)

Oxy-/amino-difluoromethylthiolation of β,γ-unsaturated oximes/hydrazones have been developed for construction of HCF2S-containing isoxazolines and pyrazolines by employing PhSO2SCF2H as difluoromethylthiolation reagent under mild conditions. Such transformations exhibit good functional group tolerance and scalability. Possible mechanisms are proposed. 

Oxy‐/Amino‐Difluoromethylthiolation of Alkenes: Synthesis of HCF2S‐Containing Isoxazolines and Pyrazolines

Copper-Catalyzed Four-Component Cascade Reaction for the Construction of Triazoles Bearing β-Hydroxy Chalcogenides

A radical bicyclization of 2-cyanoaryl acrylamides with dicumyl peroxide has been developed for constructing a broad spectrum of benzo[h]naphtho[1,8-bc][1,6]naphthyridine. This reaction allows the formation of three new chemical bonds through addition of methyl radical across alkene double bond, intramolecular addition of carbon-centered radical to cyano group and cyclization of the iminyl radical cascade, and features simple reaction system and wide substrate scope. 

Bo-Xun Sun

Papers

Oxy‐/Amino‐Difluoromethylthiolation of Alkenes: Synthesis of HCF2S‐Containing Isoxazolines and Pyrazolines

Copper-Catalyzed Four-Component Cascade Reaction for the Construction of Triazoles Bearing β-Hydroxy Chalcogenides

Oxidative Dehydrogenative Coupling of Thiols with Alkanes for the Synthesis of Sulfoxides.

Copper-Catalyzed Cascade Multicomponent Reaction of Azides, Alkynes, and Selenium: Synthesis of Ditriazolyl Diselenides.

Radical Bicyclization of 2‐Cyanoaryl Acrylamides with Dicumyl Peroxide