Pd‐Catalyzed Intermolecular Transthiolation of Ar‐OTf Using Methyl 3‐(Methylthio) Propanoate as a Thiol Surrogate

Pan, Dandan; Xu, Shasha; Tian, Qingqiang; Li, Yahui

doi:10.1002/ejoc.202100822

Cited by 2 publications

(1 citation statement)

References 23 publications

(8 reference statements)

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“…225 A large series of alkylaryl sulfides (20 examples) were obtained in 56−88% yields via the Pd(TFA) 2 /Xantphoscatalyzed reaction of aryl triflates with methyl (3-alkylthio)propanoate as a source of the AlkS group. 226 2,2-Diphenyl-1,3oxathiolane was used as a vinyl sulfide surrogate for the preparation of arylvinyl sulfides (Scheme 31). 227 Vinyl sulfide is generated under basic conditions.…”

Section: Catalytic Cross-coupling Reactions (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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Section: Catalytic Cross-coupling Reactions (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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Expanding the Use of Benzothioxanthene Imides to Photochemistry: Eco‐Friendly Aerobic Oxidation of Sulfides to Sulfoxides

Serviou,

Gkizis,

Sánchez

et al. 2024

ChemSusChem

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The sulfoxide moiety is one of the most commonly utilized groups in pharmaceutical and industrial chemistry. The need for sustainability and easy accessibility to sulfoxide moieties is deemed necessary, due to its ubiquity in natural products and potentially pharmaceutically active compounds. In this context, we report herein a sustainable, aerobic and environmentally friendly photochemical protocol based on the use of a benzothioxathene imide as the photocatalyst to selectively oxidise sulfides under mild irradiation (456 nm), in very low catalyst loading (0.01 mol%) and on water. In addition, to demonstrate the compatibility of our protocol with wide scope of substrates, the latter was successfully applied to the synthesis of the biologically‐active Sulforaphane and Modafinil.

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Pd‐Catalyzed Intermolecular Transthiolation of Ar‐OTf Using Methyl 3‐(Methylthio) Propanoate as a Thiol Surrogate

Cited by 2 publications

References 23 publications

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

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

Expanding the Use of Benzothioxanthene Imides to Photochemistry: Eco‐Friendly Aerobic Oxidation of Sulfides to Sulfoxides

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