Alternative synthetic routes to hydrofluoroolefins

Yagupolskii, Yurii L.; Pavlenko, N. V.; Shelyazhenko, S. V.; Filatov, Andrey A.; Kremlev, M. M.; Mushta, A. I.; Gerus, Igor I.; Peng, Sheng; Петров, В. А.; Nappa, Mario J.

doi:10.1016/j.jfluchem.2015.08.001

Cited by 23 publications

(11 citation statements)

References 27 publications

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“…[7b] Olefinic or aromatic CÀFbonds do notreactat ACFi nt he presence of silaneso rg ermanes. [11] Scarce reactivity studieso f1 includer eactions towardsa lkoxides, [12] alcohols, [13] ando xidative Heck reactionsw itha rylb oronic acids. [9] Thep olyfluorinated olefinsH FO-1234yf( 1;2 ,3,3,3-tetrafluoropropene) andH FO-1234ze( 2;1 ,3,3,3-tetrafluoropropene)a re very interestings ubstrates fort he synthesiso f fluorinatedb uildingb lockso fh igherv alue.B ecause of their lowg lobalw arming potential, they areu sefuls ubstitutes for HFO-134a (1,1,1,2-tetrafluoroethane) as refrigerants.…”

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confidence: 99%

“…[10] However,the decompositionofHFO-1234yf(1)inthe atmosphere or at high temperatures is also amatterofdiscussion. [11] Scarce reactivity studieso f1 includer eactions towardsa lkoxides, [12] alcohols, [13] ando xidative Heck reactionsw itha rylb oronic acids. [14] HFO-1234ze (2), whichi sa ni somero fH FO-1234yf (1), waso nlya pplied in hydrosilylationr eactions with HSiCl 3 , [15] andp atents coverthe addition of HF,C l 2 ,o rH 2 .…”

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confidence: 99%

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Consecutive Transformations of Tetrafluoropropenes: Hydrogermylation and Catalytic C−F Activation Steps at a Lewis Acidic Aluminum Fluoride

et al. 2017

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Functionalization reactions of the refrigerants HFO-1234yf (2,3,3,3-tetrafluoropropene) and HFO-1234ze (1,3,3,3-tetrafluoropropene) were developed. The selectivity and reactivity towards CF groups of C-F activation reactions can be controlled by employing either a germane or a silane as the hydrogen source. Unique transformations were designed to accomplish consecutive hydrogermylation and C-F activation steps. This allowed for an unprecedented transformation of an olefinic C-F bond into a C-H bond by heterogeneous catalysis. These reactions are catalyzed by nanoscopic aluminum chlorofluoride (ACF) under very mild conditions.

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confidence: 99%

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confidence: 99%

Consecutive Transformations of Tetrafluoropropenes: Hydrogermylation and Catalytic C−F Activation Steps at a Lewis Acidic Aluminum Fluoride

et al. 2017

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“…However, the decomposition of HFO‐1234yf ( 1 ) in the atmosphere or at high temperatures is also a matter of discussion . Scarce reactivity studies of 1 include reactions towards alkoxides, alcohols, and oxidative Heck reactions with aryl boronic acids . HFO‐1234ze ( 2 ), which is an isomer of HFO‐1234yf ( 1 ), was only applied in hydrosilylation reactions with HSiCl 3 , and patents cover the addition of HF, Cl 2 , or H 2…”

Section: Methodsmentioning

confidence: 99%

Consecutive Transformations of Tetrafluoropropenes: Hydrogermylation and Catalytic C−F Activation Steps at a Lewis Acidic Aluminum Fluoride

et al. 2017

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Functionalization reactions of the refrigerants HFO‐1234yf (2,3,3,3‐tetrafluoropropene) and HFO‐1234ze (1,3,3,3‐tetrafluoropropene) were developed. The selectivity and reactivity towards CF3 groups of C−F activation reactions can be controlled by employing either a germane or a silane as the hydrogen source. Unique transformations were designed to accomplish consecutive hydrogermylation and C−F activation steps. This allowed for an unprecedented transformation of an olefinic C−F bond into a C−H bond by heterogeneous catalysis. These reactions are catalyzed by nanoscopic aluminum chlorofluoride (ACF) under very mild conditions.

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“…Solid Lewis acids with a high fluoride ion affinity as catalysts are useful tools for C–F bond activation reactions since the Lewis acidic centers can induce dehydrofluorination reactions, involving the abstraction of a fluoride ion by heterolytic bond cleavage [ 28 – 31 ]. AlF 3 -based catalysts are among the strongest Lewis acidic materials.…”

Section: Introductionmentioning

confidence: 99%

Activation of pentafluoropropane isomers at a nanoscopic aluminum chlorofluoride: hydrodefluorination versus dehydrofluorination

Kervarec

Braun

Ahrens

et al. 2020

Beilstein J. Org. Chem.

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The hydrofluorocarbon 245 isomers, 1,1,1,3,3-pentafluoropropane, 1,1,1,2,2- pentafluoropropane, and 1,1,1,2,3-pentafluoropropane (HFC-245fa, HFC-245cb, and HFC-245eb) were activated through C–F bond activations using aluminium chlorofluoride (ACF) as a catalyst. The addition of the hydrogen source Et3SiH is necessary for the activation of the secondary and tertiary C–F bonds. Multiple C–F bond activations such as hydrodefluorinations and dehydrofluorinations were observed, followed by hydroarylation and Friedel–Crafts-type reactions under mild conditions.

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Alternative synthetic routes to hydrofluoroolefins

Cited by 23 publications

References 27 publications

Consecutive Transformations of Tetrafluoropropenes: Hydrogermylation and Catalytic C−F Activation Steps at a Lewis Acidic Aluminum Fluoride

Consecutive Transformations of Tetrafluoropropenes: Hydrogermylation and Catalytic C−F Activation Steps at a Lewis Acidic Aluminum Fluoride

Consecutive Transformations of Tetrafluoropropenes: Hydrogermylation and Catalytic C−F Activation Steps at a Lewis Acidic Aluminum Fluoride

Activation of pentafluoropropane isomers at a nanoscopic aluminum chlorofluoride: hydrodefluorination versus dehydrofluorination

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