Palladium and copper co-catalyzed Markovnikov hydrothiolation of terminal olefins and alkynes

Ma, Haojie; Ren, Xiaoyu; Zhou, Xiaoqiang; Ma, Chaowei; He, Yu; Huang, Guosheng

doi:10.1016/j.tetlet.2015.09.047

Cited by 17 publications

(6 citation statements)

References 40 publications

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“…The thiol-yne click (TYC) reaction, also known as alkyne hydrothiolation, is one of the simplest and most atom-economical approach to produce alkenyl sulfides from thiols and alkynes. 4,5 The TYC reaction commonly occurs in the presence of free radicals, 6 strong acids, 7 bases 8 or transition metals 9 and, as shown in Scheme 1 , in principle can lead to one of the regio- and stereoisomeric vinyl sulfides: A (branched) through a Markovnikov orientation, B (E linear) and C (Z linear), or produce mixtures of them through an anti-Markovnikov orientation ( Scheme 1 ). 10,11 …”

Section: Introductionmentioning

confidence: 99%

Thiol-yne click reaction: an interesting way to derive thiol-provided catechols

et al. 2021

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Section: Introductionmentioning

confidence: 99%

Thiol-yne click reaction: an interesting way to derive thiol-provided catechols

et al. 2021

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“…This, also called a thiol–ene “click” reaction, has been exploited as a synthetic tool mostly in materials chemistry . In contrast, an acid- or metal-catalyzed cationic pathway usually provides the Markovnikov product …”

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confidence: 99%

Palladium-Catalyzed Tandem Isomerization/Hydrothiolation of Allylarenes

Kathe

Fleischer

2019

Org. Lett.

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Herein we report a tandem olefin migration/hydrothiolation of allyl benzenes facilitated by an in situ generated palladium hydride. A catalyst system composed of palladium acetate and bidentate ligand dtbpx (1,2-bis(di-tert-butylphosphinomethyl)benzene in the presence of catalytic amounts of triflic acid led to the tandem transformation, which furnished benzylic thioethers. The reaction exhibits high regioselectivity and can be conducted under mild conditions. The robustness of the catalyst is displayed through reactions with coordinating thiols.

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“…903 Palladium acetate as a catalyst (2 mol %) and Cu(OTf) 2 as an additive (5 mol %) were studied for performing the hydrothiolation process in a bimetallic system (Scheme 282). 904 A copper salt was proposed to facilitate the coordination of a carbon−carbon multiple bond to the palladium center, where actual hydrothiolation took place.…”

Section: Palladium-catalyzed Transformationsmentioning

confidence: 99%

“…Palladium acetate as a catalyst (2 mol %) and Cu(OTf) 2 as an additive (5 mol %) were studied for performing the hydrothiolation process in a bimetallic system (Scheme ). A copper salt was proposed to facilitate the coordination of a carbon–carbon multiple bond to the palladium center, where actual hydrothiolation took place. The system was efficient not only in the hydrothiolation of terminal alkynes leading to vinyl sulfides but also in the hydrothiolation of terminal olefins resulting in alkyl sulfides (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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Palladium and copper co-catalyzed Markovnikov hydrothiolation of terminal olefins and alkynes

Cited by 17 publications

References 40 publications

Thiol-yne click reaction: an interesting way to derive thiol-provided catechols

Thiol-yne click reaction: an interesting way to derive thiol-provided catechols

Palladium-Catalyzed Tandem Isomerization/Hydrothiolation of Allylarenes

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

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