Indium(<scp>iii</scp>) catalysed regio- and stereoselective hydrothiolation of bromoalkynes

Rajesh, Nimmakuri; Prajapati, Dipak

doi:10.1039/c4ra04359f

Cited by 22 publications

(6 citation statements)

References 54 publications

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“…In fact, only three examples involving metal catalysts have been reported to date. In one of them, indium(III) trifluoromethanesulfonate was found to catalyze the regioselective anti addition of different heterocyclic thiols to aromatic and aliphatic bromoalkynes, generating the corresponding ( Z )‐β‐bromo vinyl sulfides in good yields (Scheme ) . Attempts to add aromatic and aliphatic thiols failed, and only the formation of disulfide products via homocoupling of the thiols was in these cases observed.…”

Section: S–h Bond Addition Reactionsmentioning

confidence: 99%

Metal‐Catalyzed Hydrofunctionalization Reactions of Haloalkynes

Cadierno

2019

Eur J Inorg Chem

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Metal‐catalyzed hydrofunctionalization reactions of alkynes, i.e. the addition of E–H units (E = heteroatom or carbon) across the C≡C bond, are of key importance in modern synthetic chemistry. In recent years, haloalkynes have been successfully involved in these types of transformations, thus opening new atom‐economical routes for the generation, among others, of haloalkenes, a pivotal class of compounds for cross‐coupling processes. In particular, several catalytic systems able to promote the selective addition of C–H, O–H, N–H, S–H and X–H (X = halide) bonds to haloalkynes have been reported. This chemistry is comprehensively discussed in this Minireview article.

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Section: S–h Bond Addition Reactionsmentioning

confidence: 99%

Metal‐Catalyzed Hydrofunctionalization Reactions of Haloalkynes

Cadierno

2019

Eur J Inorg Chem

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“…Selective hydrothiolation of bromoalkynes was performed with an indium catalyst (Scheme ). The reaction was tolerant to the presence of C( SP )–Br and C( SP2 )–Br halogen atoms. Addition of thiols to allenols led to the C–S bond formation, and the process was accompanied by elimination of water (Scheme ).…”

Section: Catalytic Z–h Bond Addition Reactions (Z = S Se Te)mentioning

confidence: 99%

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

2022

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In the present review, we discuss recent progress in the field of C–Z bond formation reactions (Z = S, Se, Te) catalyzed by transition metals. Two complementary methodologies are consideredcatalytic cross-coupling reactions and catalytic addition reactions. The development of advanced catalytic systems is aimed at improved catalyst efficiency, reduced catalyst loading, better cost efficiency, environmental concerns, and higher selectivity and yields. The important rise of research efforts in sustainability and green chemistry areas is critically assessed. The paramount role of mechanistic studies in the development of a new generation of catalytic systems is addressed, and the key achievements, problems, and challenges are summarized for this field.

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“…24 Scheme 14 In(OTf) 3 -catalyzed hydrothiolation of terminal alkynes 24 Internal alkynes were generally not tolerated, but the method could be extended to 1-bromoalkynes with heteroaromatic thiols, yielding predominantly Z-alkenes. 25…”

Section: Short Review Syn Thesismentioning

confidence: 99%

Indium(III)-Catalyzed Transformations of Alkynes: Recent Advances in Carbo- and Heterocyclization Reactions

2017

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The use of a well-chosen catalyst is instrumental for the development of more efficient, economical and environmentally friendly reactions. In recent decades, indium-based catalysts have proven to be competitive and useful alternatives to transition-metal catalysts such as silver and gold. In this short review, we present some of the recent advances in indium(III)-catalyzed transformations of alkynes, with a focus on cyclization reactions.1 Introduction2 Terminal Alkynes as Nucleophiles3 Nucleophilic Additions to Alkynes4 Carbo- and Heterocyclization Reactions4.1 Carbocyclization4.2 Oxygen-Based Heterocycles4.3 Nitrogen-Based Heterocycles4.4 Sulfur-Based Heterocycles5 Conclusion

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Indium(iii) catalysed regio- and stereoselective hydrothiolation of bromoalkynes

Cited by 22 publications

References 54 publications

Metal‐Catalyzed Hydrofunctionalization Reactions of Haloalkynes

Metal‐Catalyzed Hydrofunctionalization Reactions of Haloalkynes

Transition-Metal-Catalyzed C–S, C–Se, and C–Te Bond Formations via Cross-Coupling and Atom-Economic Addition Reactions. Achievements and Challenges

Indium(III)-Catalyzed Transformations of Alkynes: Recent Advances in Carbo- and Heterocyclization Reactions

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