Addition reaction of 3,3,3-trifluoropropene to tetrahydrofuran. Telomeric growth via free-radical rearrangements

Bergstrom, Donald E.; Ng, Mae W.; Wong, James J.

doi:10.1039/p19830000741

Cited by 14 publications

(3 citation statements)

References 3 publications

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“…On the basis of these results and previous findings in another group, our proposed radical mechanism is shown in Scheme . Initially, a trace amount of inevitable and/or adventitious oxygen generated the corresponding THF radical 4 .…”

supporting

confidence: 72%

Property and Reactivity of Fluoro(silyl)acetylenes and Fluoro(stannyl)acetylenes

2010

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supporting

confidence: 72%

Property and Reactivity of Fluoro(silyl)acetylenes and Fluoro(stannyl)acetylenes

2010

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“…Trifluoromethyl-substituted alkenes 2 were initially selected for exploring the proposed cyclopropanation given their known compatibility with photoredox catalysis and proficiency as radical acceptors. , In addition, success here would allow the mild, one-step preparation of valuable TFCps 3 from trifluoromethyl-substituted alkenes. Given the ease with which these olefins can now easily be accessed from commercially available trifluoromethyl ketones, aryl halides, or organoboron reagents, success here would provide a regiospecific means to install the TFCp motif on virtually any scaffold (arene, hetereoarene, aliphatic, etc., Figure ).…”

Section: Discussionmentioning

confidence: 99%

Redox-Neutral Photocatalytic Cyclopropanation via Radical/Polar Crossover

et al. 2018

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A benchtop stable, bifunctional reagent for the redox-neutral cyclopropanation of olefins has been developed. Triethylammonium bis(catecholato)iodomethylsilicate can be readily prepared on multigram scale. Using this reagent in combination with an organic photocatalyst and visible light, cyclopropanation of an array of olefins, including trifluoromethyl- and pinacolatoboryl-substituted alkenes, can be accomplished in a matter of hours. The reaction is highly tolerant of traditionally reactive functional groups (carboxylic acids, basic heterocycles, alkyl halides, etc.) and permits the chemoselective cyclopropanation of polyolefinated compounds. Mechanistic interrogation revealed that the reaction proceeds via a rapid anionic 3- exo- tet ring closure, a pathway consistent with experimental and computational data.

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“…The reactions of 563 with strong electrophiles occur slowly under rather severe conditions, providing addition products that arise from attacking electrophiles at R-position via 566 (Scheme 159). 272 The reactions of 3,3,3-trifluoropropene (568) with radicals proceed mostly via radical addition at β-position followed by hydrogen abstraction (Scheme 160), 273 where no defluorination is observed.…”

Section: S N 2′ Type Reactions In Trifluoromethylalkenesmentioning

confidence: 99%