scholarly journals Synthesis of benzyl sulfides via substitution reaction at the sulfur of phosphinic acid thioesters

2020 ◽  
Vol 56 (43) ◽  
pp. 5771-5774
Author(s):  
Yoshitake Nishiyama ◽  
Takamitsu Hosoya ◽  
Suguru Yoshida
Keyword(s):  
Substitution Reaction ◽  
Bond Formation ◽  
Phosphinic Acid ◽  
Grignard Reagents ◽  
Acid Thioesters ◽  
Sulfur Bond

An ambident electrophilicity of phosphinic acid thioesters is disclosed. Unexpected carbon–sulfur bond formation took place in the reaction between phosphinic acid thioesters and benzyl Grignard reagents to provide various benzyl sulfides.

Design and Development of Fe-Catalyzed Intra- and Intermolecular Carbofunctionalization of Vinyl Cyclopropanes

2019 ◽  
Author(s):  
Lei Liu ◽  
Wes Lee ◽  
Mingbin Yuan ◽  
Chris Acha ◽  
Michael B. Geherty ◽  
...  
Keyword(s):  
Bond Formation ◽  
Cross Coupling ◽  
Alkyl Halides ◽  
Grignard Reagents ◽  
Mechanistic Studies ◽  
Radical Intermediates ◽  
Design And Implementation ◽  
Solvent Cage ◽  
Radical Cascade ◽  
Radical Processes

Design and implementation of the first (asymmetric) Fe-catalyzed intra- and intermolecular difunctionalization of vinyl cyclopropanes (VCPs) with alkyl halides and aryl Grignard reagents has been realized via a mechanistically driven approach. Mechanistic studies support the diffusion of the alkyl radical intermediates out of the solvent cage to participate in an intra- or -intermolecular radical cascade with the VCP followed by re-entering the Fe radical cross-coupling cycle to undergo selective C(sp2)-C(sp3) bond formation. Overall, we provide new design principles for Fe-mediated radical processes and underscore the potential of using combined computations and experiments to accelerate the development of challenging transformations.

scholarly journals Lewis acid / Base-free Strategy for the Synthesis of 2-Arylthio and Selenyl Benzothiazole / Thiazole and Imidazole

2021 ◽  
Vol 27 (1) ◽  
pp. 17-23
Author(s):  
Guniganti Balakishan ◽  
Gullapalli Kumaraswamy ◽  
Vykunthapu Narayanarao ◽  
Pagilla Shankaraiah
Keyword(s):  
Lewis Acid ◽  
Bond Formation ◽  
Acid Base ◽  
Mechanistic Pathway ◽  
Wide Range ◽  
Acid And Base ◽  
Lewis Acid And Base ◽  
Sulfur Bond

Abstract A Cu(II)-catalyzed Csp2-Se and Csp2-Sulfur bond formation was achieved with moderate to good yields without the aid of Lewis acid and base. The reaction is compatible with a wide range of heterocycles such as benzothiazole, thiazole, and imidazole. Also, this typical protocol is found to be active in thio-selenation via S-H activation. Additionally, we proposed a plausible mechanistic pathway involving Cu(III) putative intermediate.

scholarly journals Carbon–sulfur bond formation by reductive elimination of gold(iii) thiolates

2018 ◽  
Vol 47 (18) ◽  
pp. 6333-6343 ◽  
Author(s):  
Lucy Currie ◽  
Luca Rocchigiani ◽  
David L. Hughes ◽  
Manfred Bochmann
Keyword(s):  
Bond Formation ◽  
Reductive Elimination ◽  
Pincer Complexes ◽  
Elimination Reactions ◽  
Sulfur Bond

Thiols were found to cleave Au–C bonds in (C^N^C)gold(iii) pincer complexes and to induce C–S reductive elimination reactions, to give aryl thioethers.

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