The first example of transition-metal-catalyzed addition of aromatic thiols to acetylenes

Kuniyasu, Hitoshi; Ogawa, Akira; Sato, Kyosuke; Ryu, Ilhyong; Kambe, Nobuaki; Sonoda, Noboru

doi:10.1021/ja00040a087

Cited by 230 publications

(104 citation statements)

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“…The extensive studies on the thiol-yne reaction in the past half century have revealed that they proceed through Markovnikov and anti-Markovnikov addition routes to yield regioand stereo-isomers with branched and linear structures (Figure 1) [41][42][43]. Besides the radical and amine-mediated reactions, the transition-metal complexes could catalyze the thiol-yne reaction and have been proven to be efficient catalysts for the preparation of regio-and stereo-regular vinyl sulfides.…”

Section: Transition-metal-catalyzed Thiol-yne Click Polymerizationmentioning

confidence: 99%

Thiol-yne click polymerization

et al. 2013

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The research on using thiol-ene click reaction to synthesize sulfur-containing polymers with topological structures and advanced functional properties is a hot topic. However, the application of the thiol-yne reaction in the functional polymer preparation is limited and the thiol-yne click polymerization is to be further developed. In this review, we summarized recent research efforts on using thiol-yne click polymerization to synthesize polymers with topological structures. The sulfur-containing polymers were facilely prepared by photo-and thermo-initiated, amine-mediated, and transition-metal-catalyzed thiol-yne click polymerizations. These polymers are promising to be used as drug-delivery vehicles, high refractive index optical materials, photovoltaic materials, and biomaterials etc.thiol-yne click polymerization, radical mechanism, amine, rhodium complex, function Citation:

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Section: Transition-metal-catalyzed Thiol-yne Click Polymerizationmentioning

confidence: 99%

Thiol-yne click polymerization

et al. 2013

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“…[50,51] ArSH addition to terminal alkynes was carried out with 55-87 % product yields and Ͼ11:1 selectivities with regard to Markovnikov/antiMarkovnikov products (THF, 67°C, 12-16 h). Depending on reaction temperature, up to 14 % of 14 was obtained due to an isomerization side-reaction.…”

Section: Pd- Pt- and Rh-catalyzed E-h Bond Additions To Alkynesmentioning

confidence: 99%

Unusual Influence of the Structures of Transition Metal Complexes on Catalytic C–S and C–Se Bond Formation Under Homogeneous and Heterogeneous Conditions

2007

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In the presence of transition metal catalysts, hydrothiolation and hydroselenation reactions, as well as bisthiolation and bisselenation reactions, have been successfully carried out with high selectivities and yields. New transition metal-catalyzed synthetic methods have been developed for the preparation of vinyl sulfides and vinyl selenides of various types. Mechanistic study has revealed that a homogeneous catalytic system based on phosphine complexes of palladium is the

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“…In the final stage, reductive 22 A. Ishii In the hydrosilylation, theoretical study on the reaction of PtH(SiR 3 )PH 3 with ethylene showed that ethylene is inserted into the Pt-H bond with a lower activation energy than into the Pt-SiR 3 bond [9].…”

Section: M]-h Insertion (Hydrometalation) To Give [M](er)(vinyl) and mentioning

confidence: 99%

The Mechanism for Transition-Metal-Catalyzed Hydrochalcogenation of Unsaturated Organic Molecules

Ishii

Nakata

2011

Hydrofunctionalization

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In this chapter, discussions are focused on two types of mechanisms of transition-metal-catalyzed hydrochalcogenation, Type I and Type II, which are classified by the initial behavior of precatalysts. In Type I mechanism, precatalyst M-X (M ¼ Pd, Ni, Zr, Ln, and An) first undergoes protonolysis with REH (E ¼ O, S, and Se) to generate active catalyst M-ER, which then undergoes insertion of alkyne into the M-ER bond (chalcogenometalation) to give 2-chalcogenovinyl complex, followed by protonolysis of M-C vinyl with REH to produce the product and to regenerate active catalyst M-ER. Type II mechanism starts from oxidative addition of REH (E ¼ S and Se) to

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The first example of transition-metal-catalyzed addition of aromatic thiols to acetylenes

Cited by 230 publications

References 0 publications

Thiol-yne click polymerization

Thiol-yne click polymerization

Unusual Influence of the Structures of Transition Metal Complexes on Catalytic C–S and C–Se Bond Formation Under Homogeneous and Heterogeneous Conditions

The Mechanism for Transition-Metal-Catalyzed Hydrochalcogenation of Unsaturated Organic Molecules

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