ChemInform Abstract: A Prototype of Transition‐Metal‐Catalyzed Carbothiolation of Alkynes.

Sugoh, Kunihiko; Kuniyasu, Hitoshi; Sugae, Taeko; Ohtaka, Atsushi; Takai, Yasutomo; Tanaka, Atsunori; Machino, Chikako; Kambe, Nobuaki

doi:10.1002/chin.200138092

ChemInform

2001

DOI: 10.1002/chin.200138092

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ChemInform Abstract: A Prototype of Transition‐Metal‐Catalyzed Carbothiolation of Alkynes.

Kunihiko Sugoh

Hitoshi Kuniyasu

Taeko Sugae

et al.

Abstract: A Prototype of Transition-Metal-Catalyzed Carbothiolation of Alkynes.-A novel method for the regio-and stereoselective addition of carbon and sulfur functionalities to alkynes is developed.-(SUGOH,

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“…Herein we report a nickel-catalyzed syn-selective 1,2-carbosulfenylation reaction [29][30][31] of simple unactivated alkenes 32 . Critical to the success of this reaction is the identification of N-sulfenyl-N-alkyl sulfonamides as N-S electrophiles.…”

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confidence: 99%

Electrophilic Sulfur Reagent Design Enables Catalytic syn-Carbosulfenylation of Unactivated Alkenes

Yi-lin

Kang

et al. 2021

Preprint

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A multi-component approach to structurally complex organosulfur products is described via the nickel-catalyzed 1,2-carbosulfenylation of unactivated alkenes with organoboron nucleophiles and tailored organosulfur electrophiles. Key to the development of this transformation is the identification of a modular N-alkyl-N-(arylsulfenyl)arenesulfonamide family of sulfur electrophiles. Tuning the electronic and steric properties of the leaving group in these reagents controls pathway selectivity, favoring three-component coupling and suppressing side reactions, as examined via computational studies. The unique syn-stereoselectivity differs from traditional electrophilic sulfenyl transfer processes involving a thiiranium ion intermediate and arises from the directed arylnickel(I) migratory insertion mechanism, as elucidated through reaction kinetics and control experiments. Reactivity and regioselectivity are facilitated by a collection of monodentate, weakly coordinating native directing groups, including sulfonamides, alcohols, amines, amides, and azaheterocycles.

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mentioning

confidence: 99%

Electrophilic Sulfur Reagent Design Enables Catalytic syn-Carbosulfenylation of Unactivated Alkenes

Yi-lin

Kang

et al. 2021

Preprint

View full text Add to dashboard Cite

show abstract

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ChemInform Abstract: A Prototype of Transition‐Metal‐Catalyzed Carbothiolation of Alkynes.

Abstract: A Prototype of Transition-Metal-Catalyzed Carbothiolation of Alkynes.-A novel method for the regio-and stereoselective addition of carbon and sulfur functionalities to alkynes is developed.-(SUGOH,

Cited by 1 publication

References 1 publication

Electrophilic Sulfur Reagent Design Enables Catalytic syn-Carbosulfenylation of Unactivated Alkenes

Electrophilic Sulfur Reagent Design Enables Catalytic syn-Carbosulfenylation of Unactivated Alkenes

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