Palladium-Catalyzed Regioselective Addition of Thiophenol to Conjugated Enynes. Efficient Syntheses of 2-(Phenylsulfinyl) and 2-(Phenylsulfonyl) 1,3-Dienes

Baeckvall, Jan‐E.; Ericsson, Anna

doi:10.1021/jo00099a003

Cited by 109 publications

(39 citation statements)

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“…As such, vinyl sulfones have been incorporated into a variety of drugs aimed at enzyme inhibition through irreversible reaction between catalytic residues within the active site and the vinyl sulfone moiety . Vinyl sulfones can be easily obtained from vinyl sulfides through simple oxidation …”

Section: Hydrothiolation Of Alkynesmentioning

confidence: 99%

Hydroelementation of Unsaturated C–C Bonds Catalyzed by Metal Scorpionate Complexes

Wathier

Love

2016

Eur J Inorg Chem

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Tridentate scorpionate ligands have a rich history in coordination chemistry. In the past two decades, metal complexes bearing scorpionate ligands have found increasing utility as catalysts for a variety of useful transformations. This microreview focuses on the utility of scorpionate ligands in hydro- [a] 2396 Scheme 13. Proposed mechanism for To M Mg-mediated aminoalkene hydroamination (see ref. [54] ).

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Section: Hydrothiolation Of Alkynesmentioning

confidence: 99%

Hydroelementation of Unsaturated C–C Bonds Catalyzed by Metal Scorpionate Complexes

Wathier

Love

2016

Eur J Inorg Chem

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“…Soon after,t he scope of alkynes was extended to conjugated enynes. [11] Use of 2-10 mol. %o fP d(OAc) 2 resulted in exclu-Scheme1.Overview of the transition-metal catalyzed reactionso fZ ÀHa nd ZÀZ( Z =S, Se) bonds with alkynes discussed in the review.…”

Section: Catalytic Systems Leadingt Om Arkovnikov-type (Branched)vinymentioning

confidence: 99%

Metal Catalysis in Thiolation and Selenation Reactions of Alkynes Leading to Chalcogen-Substituted Alkenes and Dienes

Orlov

2015

ChemistryOpen

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This review covers recent achievements in metal‐catalyzed Z−H and Z−Z (Z=S, Se) bond addition to the triple bonds of alkynes—a convenient and atom‐efficient way to carbon‐element bond formation. Various catalytic systems (both homogeneous and heterogeneous) developed to date to obtain mono‐ and bis‐chalcogen‐substituted alkenes or dienes, as well as carbonyl compounds or heterocycles, starting from simple and available alkynes and chalcogenols or dichalcogenides are described. The right choice of metal and ligands allows us to perform these transformations with high selectivities under mild reaction conditions, thus tolerating unprotected functional groups in substrates and broadening ways of further modification of the products. The main aim of the review is to show the potential of the catalytic methods developed in synthetic organic chemistry. Thus, emphasis is made on the scope of reactions, types of products that can be selectively formed, convenience, and scalability of the catalytic procedures. A brief mechanistic description is also given to introduce new readers to the topic.

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“…For example, the palladium-catalyzed hydrothiolation of conjugated enynes affords a series of 2-(phenylsulfanyl)-1,3-dienes regioselectively in good yields (Scheme 29) [100]. Palladium-catalyzed hydrothiolation of alkynylphosphines proceeds via antiaddition process, yielding the corresponding (Z)-1-phosphino-2-thioalkenes regioand stereoselectively.…”

Section: Applications To the Synthesis Of Functionalized Sulfur Compomentioning

confidence: 99%

Transition-Metal-Catalyzed S–H and Se–H Bonds Addition to Unsaturated Molecules

Ogawa

2011

Hydrofunctionalization

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This chapter deals with the transition-metal-catalyzed hydrothiolation and hydroselenation of alkynes and allenes and related unsaturated compounds with thiols and selenols. In these reactions, the regio-and/or stereoselectivities of the addition products can be controlled by switching the transition metal catalysts. Metal sulfides and selenides (RE-ML n , E ¼ S, Se, M ¼ Ni, Pd, Rh, Zr, Sm, etc.) play an important role as key catalyst species in these hydrothiolation and hydroselenation. The introduction of carbon monoxide into these hydrothiolation and hydroselenation systems leads to novel carbonylation with simultaneous addition of thio and seleno groups to unsaturated bonds.

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Palladium-Catalyzed Regioselective Addition of Thiophenol to Conjugated Enynes. Efficient Syntheses of 2-(Phenylsulfinyl) and 2-(Phenylsulfonyl) 1,3-Dienes

Cited by 109 publications

References 0 publications

Hydroelementation of Unsaturated C–C Bonds Catalyzed by Metal Scorpionate Complexes

Hydroelementation of Unsaturated C–C Bonds Catalyzed by Metal Scorpionate Complexes

Metal Catalysis in Thiolation and Selenation Reactions of Alkynes Leading to Chalcogen-Substituted Alkenes and Dienes

Transition-Metal-Catalyzed S–H and Se–H Bonds Addition to Unsaturated Molecules

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