Synthesis of cyclic sulfides by nickel complexes catalyzed electroreduction of unsaturated thioacetates and thiosulfonates

Ozaki, Shigeko; Matsui, Eiki; Saiki, Toyokazu; Yoshinaga, Hideaki; Ohmori, Hidenobu

doi:10.1016/s0040-4039(98)01802-4

Cited by 28 publications

(9 citation statements)

References 17 publications

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“…One example of a 2-benzylidenethietane 567 was prepared in 82% yield from 1-phenylhex-1-en-4-ylthioacetate (565) via a nickel complex-catalyzed electroreduction [161] (Scheme 129). However, the electrochemical synthetic method was widely applied for the synthesis of thiacyclopetanes and thiacyclohexanes [161].…”

Section: Synthesis Via Nucleophilic Additionmentioning

confidence: 99%

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

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Thietanes are important aliphatic four-membered thiaheterocycles that are found in the pharmaceutical core and structural motifs of some biological compounds. They are also useful intermediates in organic synthesis. Various synthetic methods of thietanes have been developed, including inter- and intramolecular nucleophilic thioetherifications, photochemical [2 + 2] cycloadditions, ring expansions and contractions, nucleophilic cyclizations, and some miscellaneous methods. The recently developed methods provide some new strategies for the efficient preparation of thietanes and their derivatives. This review focuses on the synthetic methods to construct thietane backbones developed during 1966 to 2019.

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Section: Synthesis Via Nucleophilic Additionmentioning

confidence: 99%

Recent synthesis of thietanes

Xu¹

2020

Beilstein J. Org. Chem.

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“…The thio-Mitsunobu reaction applied to thioamides gives rise to the formation of a-iminothietanes (Scheme 3.147) [265]. The formation of thietanes is also possible by electroreduction in the presence of Ni(II) salem as catalyst (Scheme 3.148) [266].…”

Section: Thietanes J219mentioning

confidence: 99%

Four‐Membered Heterocycles: Structure and Reactivity

Rousseau

Robin

2011

Modern Heterocyclic Chemistry

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“…100 Five-and six-membered ring thioethers (such as 65) were obtained in good yields in electrolyses run in DMF in a divided cell. 101 These functionalised cyclic sulfides are useful intermediates for the synthesis of biologically active compounds. 102…”

Section: Electroreduction Of Organic Halides and Coupling To Carbonyl...mentioning

confidence: 99%