Category: 83706-94-9

Ishikawa, Nobuo published the artcilePreparation of trifluoromethylated allylic alcohols from trifluoroacetaldehyde and organometallic compounds, Application In Synthesis of 83706-94-9, the publication is Journal of Fluorine Chemistry (1984), 24(4), 419-30, database is CAplus.

A number of allylic alcs. bearing a CF₃ group at the α- or γ-position, and α-trifluoromethylated γ-enols and -ynols were prepared by the reaction of CF₃CHO with a variety of organometallic compounds Most of the Reformatskii- or Grignard-type reactions required promotion by ultrasound. E.g., Reformatskii-type reaction of CF₃CHO and BrCH₂CO₂Et in the presence of Zn powder and ultrasound gave CF₃CH(OH)CH₂CO₂Et, which was dehydrated, then reduced (LiAlH₄/AlCl₃) to give CF₃CH:CHCH₂OH. Also prepared were RCH:CHCH(OH)CF₃ (R = Bu, Ph), RCMe:CHCH(OH)CF₃ (same R), CF₃CH(OH)CHR¹CH:CH₂ (R¹ = H, Me, Ph), and CF₃CH(OH)CH₂CCH.

Journal of Fluorine Chemistry published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Application In Synthesis of 83706-94-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kitazume, Tomoya published the artcileUltrasound-promoted selective perfluoroalkylation on the desired position of organic molecules, HPLC of Formula: 83706-94-9, the publication is Journal of the American Chemical Society (1985), 107(18), 5186-91, database is CAplus.

Perfluoroalkylzinc iodides or bromides were prepared from perfluoroalkyl iodides or bromides and Zn powder in DMF or THF with ultrasonic irradiation, and were used as regioselective perfluoroalkylating reagents for the preparation of a wide variety of perfluoroalkylated compounds Ultrasound-promoted asym. induction with a perfluoroalkyl group on the asym. carbon was achieved by reaction of perfluoroalkyl halides with optically active enamines in the presence of zinc powder and dichlorobis(π-cyclopentadienyl)titanium.

Journal of the American Chemical Society published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, HPLC of Formula: 83706-94-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Forcellini, Elsa published the artcileSystematic study of the reactivity of (E)-4,4,4-trifluorobut-2-en-1-yl 4-methylbenzenesulfonate towards different classes of nucleophiles, Formula: C4H5F3O, the publication is Journal of Fluorine Chemistry (2015), 216-221, database is CAplus.

The alkylation of 4-phenylphenol, benzyl alc., thiols, primary and secondary amines, indole, and malonates by (E)-F₃CCH:CHCH₂OTs was studied; in most cases (4-phenylphenol, thiols, amines, malonates), alkylation of the nucleophiles was most effective using K₂CO₃ in MeCN, while none of the conditions tried were effective for indole and benzyl alc.

Journal of Fluorine Chemistry published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Formula: C4H5F3O.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kennedy, C. Rose published the artcileSynergistic Ion-Binding Catalysis Demonstrated via an Enantioselective, Catalytic [2,3]-Wittig Rearrangement, Category: alcohols-buliding-blocks, the publication is ACS Central Science (2016), 2(6), 416-423, database is CAplus and MEDLINE.

Sigmatropic rearrangements number among the most powerful complexity-building transformations in organic synthesis but have remained largely insensitive to enantioselective catalysis due to the diffuse nature of their transition structures. Here, we describe a synergistic ion-binding strategy for asym. catalysis of anionic sigmatropic rearrangements. This approach is demonstrated with the enantioselective [2,3]-Wittig rearrangement of α-allyloxy carbonyl compounds to afford highly enantioenriched homoallylic alc. products. Chiral thiourea catalysts are shown to engage reactive anions and their countercations through a cooperative set of attractive, noncovalent interactions. Catalyst structure-reactivity-selectivity relationship studies and computational analyses provide insight into catalyst-substrate interactions responsible for enantioinduction and allude to the potential generality of this catalytic strategy.

ACS Central Science published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Category: alcohols-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Reed, John H. published the artcileA 1,3,2-Diazaphospholene-Catalyzed Reductive Claisen Rearrangement, Synthetic Route of 83706-94-9, the publication is Angewandte Chemie, International Edition (2019), 58(26), 8893-8897, database is CAplus and MEDLINE.

1,3,2-Diazaphospholenes (DAPs) are an emerging class of organic hydrides. In this work, we exploited them as efficient catalysts for very mild reductive Claisen rearrangements. The method is tolerant towards a wide variety of functional groups and operates at ambient temperature Besides being enantiospecific for substrates with existing stereogenic centers, the diastereoselectivity can be switched by varying solvents and DAP catalysts. The reaction kinetics show direct rearrangements of O-bound phospholene enolates and provide a proof-of-principle for catalytic enantioselective reactions.

Angewandte Chemie, International Edition published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Synthetic Route of 83706-94-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Fanfoni, Lidia published the artcileEfficient synthesis of new fluorinated building blocks by means of hydroformylation, Quality Control of 83706-94-9, the publication is Chimia (2014), 68(6), 371-377, database is CAplus and MEDLINE.

The hydroformylation reactions of fluorinated olefins were reviewed and added new results from the research group. The particular attention is paid to the remarkable influence of organofluorine substituents on catalyst activity, regio- and stereoselectivity of the hydroformylation reaction.

Chimia published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Quality Control of 83706-94-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Hemelaere, Remy published the artcileIntroduction of the 4,4,4-Trifluorobut-2-ene Chain Exploiting a Regioselective Tsuji-Trost Reaction Catalyzed by Palladium Nanoparticles, Application of (E)-4,4,4-Trifluorobut-2-en-1-ol, the publication is Organic Letters (2015), 17(7), 1770-1773, database is CAplus and MEDLINE.

A palladium-nanoparticle-catalyzed Tsuji-Trost reaction of 4,4,4-trifluorobut-2-en-1-yl acetate and ethyl(4,4,4-trifluorobut-2-en-1-yl)carbonate was accomplished with various nucleophiles including phenols, amines, and malonates. In the case of the phenols, isomerization of the double bond in the product (up to 20%) was observed as a side reaction [e.g., reaction of carbonate I with PhOH using in situ generated Pd NPs afforded II (62%) along with isomerization byproduct III (II:III = 90:10)]. Further synthetic transformations including hydrogenation, the Diels-Alder reaction, and asym. dihydroxylation of a product were also examined

Organic Letters published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Application of (E)-4,4,4-Trifluorobut-2-en-1-ol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Paioti, Paulo H. S. published the artcileCatalytic Enantioselective Boryl and Silyl Substitution with Trifluoromethyl Alkenes: Scope, Utility, and Mechanistic Nuances of Cu-F β-Elimination, Application In Synthesis of 83706-94-9, the publication is Journal of the American Chemical Society (2019), 141(50), 19917-19934, database is CAplus and MEDLINE.

Catalytic enantioselective methods are introduced that allow access to a variety of allyl boronates and silanes that contain a difluoroalkene unit; the resulting products may be used for the preparation of organofluorine compounds in high enantiomeric purity. Also, a number of key mechanistic aspects of the transformations were studied and analyzed. Thus, 1st, an NHC-Cu-catalyzed method for boryl substitution with F₃C-substituted alkenes is introduced. These processes, unlike the previously reported strategies, are applicable to alkyl as well as aryl substituted substrates, afford allyl boronates bearing a difluoroalkene moiety (up to 98% yield and 95:5 er). Second, the corresponding silyl substitutions, the 1st reported cases of their kind, are presented (up to 94% yield and 97:3 er). Third, exptl. and computational (DFT) studies are described that shed light on key mechanistic aspects of the catalytic processes. Evidence (x-ray structures of Cu-alkyl intermediates and kinetic studies) is put forth illustrating that the initial Cu-boryl and Cu-silyl addition is significantly faster than the ensuing Cu-F elimination, and that the latter step can be facilitated by either a mild Lewis acid (e.g., a Li or Na cation) or a nucleophilic promoter (e.g., an alkoxide). These findings together with DFT studies demonstrate that Cu-F β-elimination probably proceeds with anti-stereochem. Representative cases of ways through which the new mechanistic understanding may be used to rationalize previously disclosed findings, significantly improve a transformation, or develop new diastereo- and enantioselective catalytic methods are provided. For example, an explanation is provided regarding why bisphosphine-Cu complexes do not efficiently promote boryl substitutions with aryl-substituted substrates, but the corresponding silyl substitutions are facile, and how the size of a ligand can impact regioselectivity and efficiency.

Journal of the American Chemical Society published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Application In Synthesis of 83706-94-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kojima, Ryoto published the artcileA Copper(I)-Catalyzed Enantioselective γ-Boryl Substitution of Trifluoromethyl-Substituted Alkenes: Synthesis of Enantioenriched γ,γ-gem-Difluoroallylboronates, Synthetic Route of 83706-94-9, the publication is Angewandte Chemie, International Edition (2018), 57(24), 7196-7199, database is CAplus and MEDLINE.

The first catalytic enantioselective γ-boryl substitution of CF₃-substituted alkenes is reported. A series of CF₃-substituted alkenes was treated with a diboron reagent in the presence of a copper(I)/Josiphos catalyst to afford the corresponding optically active γ,γ-gem-difluoroallylboronates in high enantioselectivity. The thus obtained products could be readily converted into the corresponding difluoromethylene-containing homoallylic alcs. using highly stereospecific allylation reactions.

Angewandte Chemie, International Edition published new progress about 83706-94-9. 83706-94-9 belongs to alcohols-buliding-blocks, auxiliary class Trifluoromethylated Building Blocks, name is (E)-4,4,4-Trifluorobut-2-en-1-ol, and the molecular formula is C4H5F3O, Synthetic Route of 83706-94-9.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts