Synthesis of 2-Aryl-3-fluoro-5-silylthiophenes via a Cascade Reactive Sequence

Hirotaki, Kensuke; Hanamoto, Takeshi

doi:10.1021/ol400141y

Cited by 32 publications

(8 citation statements)

References 35 publications

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“…Mechanistically, due to the [2,3]-sigmatropic rearrangement involving only the migration and reorganization of σ- and π-bonds, such processes should be able to tolerate a transformable vinyl bromide atom. Therefore, 2-bromo-3,3-difluoroallyl sulfides 2 , which can be easily prepared from the S N 2′-type reaction of commercially available 2-bromo-3,3,3-trifluoropropene with thiolates, were chose as the gem -difluoroallyl source.…”

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confidence: 75%

gem-Difluoroallylation of Aryl Diazoesters via Catalyst-Free, Blue-Light-Mediated Formal Doyle–Kirmse Reaction

et al. 2019

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A first example of low-energy blue-lightmediated formal Doyle−Kirmse reaction for gem-difluoroallylation of aryl diazoesters has been developed. A variety of highly functionalized gem-difluoroallyl containing esters bearing transformable sulfur and bromine groups were efficiently assembled with broad substrate scope under mild, catalyst-free, and additive-free conditions. The reaction represents a practical and environmentally friendly approach for C−CF 2 bond formation based on rearrangement strategy, which will find potential applications among drug discovery and development.

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confidence: 75%

gem-Difluoroallylation of Aryl Diazoesters via Catalyst-Free, Blue-Light-Mediated Formal Doyle–Kirmse Reaction

et al. 2019

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“…However, BTP has been rarely utilized for S N 2’‐type reactions. There are only three examples reported so far [35,46,47] …”

Section: Sn2’ Reactionsmentioning

confidence: 99%

2‐Bromo‐3,3,3‐Trifluoropropene: A Versatile Reagent for the Synthesis of Fluorinated Compounds

2022

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2‐Bromo‐3,3,3‐trifluoropropene (BTP) represents a highly valuable synthon in synthetic chemistry, and has been widely used in organic synthesis, mainly including addition reactions, cross‐coupling reactions, cycloaddition or cyclization reactions, SN2’ reactions, and Stetter reactions for the construction of various fluorinated organic compounds. In this review, we systematically summarize these reactions; their mechanisms are also discussed.

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“…In a similar vein, Hirotaki and Hanamoto have employed 2-bromo-3,3-difluoroallyl sulfides 174a-f with great success in the synthesis of a range 3-fluorothiophenes 175a-f (Table 16) [115]. These difluoroallyl sulfides may be readily synthesised from the S N 2 reaction of 2-bromo-3,3,3-trifluoropropene (173) with various thiols.…”

Section: Scheme 55mentioning

confidence: 99%