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A noveland efficient protocol for the creation of 6-amino phenanthridinederivatives by Co(acac)2-catalyzed isocyanide insertionwith 2-aryl anilines under an O2atmosphere via homolyticaromatic substitution (HAS) type C–H functionalization hasbeen developed. This reaction not only proceeds smoothly utilizingO2as the oxidant but also provides a new approach to constructphenanthridine derivatives utilizing readily available 2-aryl anilineswith isocyanides instead of 2-isocyanobiaryls with differentradical precursors. [ABSTRACT FROM AUTHOR]

A novel I2/TBHP-mediated direct oxidative diamination reaction of indoles with anilines was developed. The reaction proceeded smoothly under aqueous and open air reaction conditions. This protocol provides a practical synthetic method for the synthesis of Tryptanthrin and the construction of N–C3 linked pyrrolidinoindolines which is the core structure of Psychotrimine. [ABSTRACT FROM AUTHOR]

The article discusses the preparation and application of organondium reagents in organic synthesis of chemical compounds. It highlights the specificity and reactivity of organondium reagents when compared with other organometallic reagents which allows chemical substrate to react with specific functional groups. It mentions that the reagents also enable organic reactions to proceed with specific chemoselectivity.

A novel CuI/BF3·Et2O/O2-mediated reaction utilizing ketones and benzylamines for the construction of substituted imidazoles in one step under mild conditions has been demonstrated. This protocol involved the removal of eight hydrogen atoms, the functionalization of four C(sp3)–H bonds and three new C–N bond formations. [ABSTRACT FROM AUTHOR]

Herein, we have developed a new method for the synthesis of ((methyl-d 3 )sulfonyl)ethyne, which is cost-effective and environmentally friendly and can be synthesized at the gram level. As an ideal thiol-yne reagent, it can be reacted with various types of thiols to afford ( Z )- and ( E )-type vinyl sulfides under different conditions with high selectivity. In addition, it can complete the conformational transition from Z- to E-type products under suitable conditions, and can also carry out further derivatization smoothly. The deuterium content of all products was greater than 99%. The preliminary mechanistic studies support the visible light-mediated radical course, and herein provide a novel and efficient synthetic strategy for the direct introduction of deuterated methyl groups, enriching the methods for the construction of C-S bond-containing compounds.

Sulfone compounds and thioether compounds are two highly valuable classes of compounds, but it is challenging to prepare sulfone and thioether compounds simultaneously and efficiently. Here we report that sulfides/selenides and sulfones can be obtained simultaneously using allyl bromide/benzyl bromide-activated alkyl bromides and thiosulfonates/selenosulfonates using a nickel-catalyzed reductive coupling and S N 2 synergistic strategy, which is characterized by excellent atom and step economy, mild reaction conditions, broad functional group compatibility, and excellent yields.

A photocatalytic synthesis of thieno[3,4- c ]quinolin-4(5 H )-ones/selenopheno[3,4- c ]quinolin-4(5 H )-ones using diphenyl disulfide or diphenyl diselenide as sulfur or selenium sources was developed. Two C-S/Se bonds and one C-C bond were constructed simultaneously without transition metals and other additives.

The cross-electrophile coupling between unactivated alkyl bromides with arenesulfonyl cyanides catalyzed by Ni(acac) 2 under reductive conditions to form unsymmetrical sulfides is developed. This approach for sulfide synthesis is practical, relies on available, unfunctionalized materials such as alkyl (pseudo)halides, and is scalable. This catalytic strategy provides a complementary method for the preparation of unsymmetrical alkyl-aryl sulfides under mild conditions with good functional group tolerance.

An efficient transition-metal-free decarboxylative cyclization of N -arylacrylamides with 2,2-difluoro-2-(phenylthio)acetic acid for the construction of thiodifluoroindoleone derivatives is described. This strategy features stable and readily available substrates, mild reaction conditions, and transition-metal-free catalysts. Notably, this protocol has successfully applied to synthesis of gem -difluoroalkenes, which exist in numerous biologically active compounds.

An iron-sulfur complex formed by the simple mixture of FeCl 3 with S 3 •- generated in situ from K 2 S is developed and applied to selective aerobic oxidation of terminal alkenes. The reaction was carried out under an atmosphere of O 2 (balloon) and could proceed on a gram scale, expanding the application of S 3 •- in organic synthesis. This study also encourages us to explore the application of an Fe-S catalyst in organic reactions.

A novel visible-light-photocatalytic deuterated thiomethylation/methylselenation of aryldiazonium salts utilizing S / Se- methyl- d 3 sulfonothioate has been developed. The mild conditions and the various functional groups provide a green protocol for the efficient and rapid introduction of the S -CD 3 or Se -CD 3 group with useful levels of deuterium content (>91% D). Trideuteromethyl sulfoxides have also been successfully chemoselectively observed by simple atmospheric changes under photocatalytic conditions.

In this paper, a visible-light-promoted cross-coupling of 4-alkyl-1,4-dihydropyridines with thio-/selenium sulfonates under transition-metal-free conditions is described. This strategy features easily available substrates, mild reaction conditions, high yields, and high chemoselectivity. A novel synthetic route for the construction of a sulfide or selenide C sp3 -S or C sp3 -Se bond under transition-metal-free conditions without an additive oxidant or base is developed. This method is well extended to the synthesis of a class of thiolated or selenylated glycosides that has not been explored before. Sulfoxides were also successfully chemoselectively observed via a facile variation of the atmosphere under photocatalyzed conditions.

New practical synthesis of 2-amino-1,3-selenazole with transition metal-free multicomponent reaction is reported here. A series of 2-amino-1,3-selenazole derivatives were afforded by the nucleophilic addition of amines to isoselenocyanate formed in situ , followed by Michael addition reaction and aromatization. The products were isolated from moderate to excellent yields.

A facile synthesis of N -(carboselenoate) benzimidazolones through metal-free reactions of ortho -diisocyanoarenes with selenosulfonates is reported here. The desired products are obtained in moderate to good yields with good functional group compatibility. The ortho -diisocyanoarenes are applied to the construction of 2-benzimidazolone derivatives for the first time.

A nickel-catalyzed defluorinative reductive cross-coupling of gem -difluoroalkenes with thiosulfonate or selenosulfonates is described. The reaction involves the formation of thiolated or selenylated monofluoroolefins via regioselective C-F bond cleavage and C-S or C-Se bond formation and features easily available substrates, mild reaction conditions, and high E -selectivity. One of the derivatives by further cross coupling with PhMgBr exhibited an aggregation-induced emission enhancement effect.

A palladium catalyzed insert reaction of isocyanides to 3-arylisoxazol-5(4 H )-ones for the construction of 4-aminomethylidene isoxazolone derivates is reported. In this transformation, only the C-H bond of the methylene group was involved while the remaining ring structure was retained. In general, this work provided a new protocol for the synthesis of 4-aminomethylidene isoxazolones.

A Mn(III) mediated cascade cyclization of new designed multifunctionalized 3-isocyano-[1,1'-biphenyl]-2-carbonitrile with arylboronic acid to construct pyrrolopyridine derivatives is developed. A series of pyrroloporidine compounds have been constructed through the formation of two new C-C bonds and one C-N bond via a radical pathway.