Cited by Decatungstate-Photocatalyzed Transformations of 2-Bromo-3,3,3-trifluoropropene for Selective Synthesis of Z/E-β-CF3-Enones

Transition‐Metal‐Mediated Fluoroalkylation of Carbon Electrophiles through Cross‐Electrophile Couplings DOI

Yun‐Cheng Luo, Xingang Zhang

Chinese Journal of Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Окт. 1, 2024

Comprehensive Summary Organofluorine compounds have attracted substantial interest in life and materials sciences due to the unique properties of fluorine atom(s) that often change physicochemical biological organic molecules. Transition‐metal‐mediated cross‐electrophile coupling between carbon electrophiles fluoroalkyl has emerged as a straightforward efficient route for synthesis wide range fluoroalkylated because its synthetic convenience without tedious organometallic reagents. Moreover, alkenes or alkynes‐involved three‐component couplings provide rapid effective access carbonfunctionalized alkanes alkenes. Herein, we comprehensively summarize transition‐metal‐mediated reductive fluoroalkylation diverse through historical perspective, including trifluoromethylation, difluoroalkylation, monofluoroalkylation, so on. Different transition metals (Cu, Ni, etc .) strategies are discussed, which nickel‐catalyzed reactions represent an attractive site‐selectively organofluorine compounds. Key Scientists As early 1965, McLoughlin Thrower finished first stoichiometric copper‐mediated aromatic iodides with iodides. However, excess elevated temperature were used this method. In 1969, Kobayashi Kumadaki reported studies on trifluoromethylation halides trifluoromethyl iodide. After more than four decades, Zhang group developed β ‐fluorinated alkylation (hetero)aryl secondary alkyl bromides 2015, difluoromethylation chlorides chlorodifluoromethane ClCF 2 H 2017. The also enantioselective alkyl‐arylation 3,3,3‐trifluoropropene tertiary 2018, MacMillan novel copper/photoredox dual catalytic system aryl ( S )‐(trifluoromethyl) dimesitylsulfonium triflate presence tris‐(trimethylsilyl) silanol. They nickel/photoredox catalyzed silane. During time, Wang monofluoroalkylation monofluoroalkyl halides. From 2021 2023, same further series trifluoroalkylation aryl, alkenyl, acyl nonfluorinated alkynes could be couplings. Chu fluoroalkyl‐acylation Later, they fluoroalkyl‐arylation unactivated tethering pendant chelating group. 2019, Chaładaj palladium‐catalyzed perfluoroalkyl‐arylation perfluoroalkyl

Язык: Английский

Процитировано

Rhodium- and Iridium-Catalyzed (Enantioselective) Fluoroamidation of gem-Difluoroalkenes via Chelation Assistance DOI

Heng Song,

Ruijie Mi,

Xingwei Li

и другие.

ACS Catalysis, Год журнала: 2025, Номер unknown, С. 6555 - 6562

Опубликована: Апрель 7, 2025

Язык: Английский

Процитировано

Synthesis of 2‐(β‐Trifluoromethyl‐β‐arylethylthio)pyridine through DBU‐Mediated Regioselective Addition of Pyridine‐2(1H)‐thione Onto α‐(Trifluoromethyl)styrenes DOI

Pai Zheng,

Yupian Deng,

Jingjing He

и другие.

Asian Journal of Organic Chemistry, Год журнала: 2024, Номер 13(3)

Опубликована: Янв. 8, 2024

Abstract An efficient and practical method for the synthesis of (β‐trifluoromethyl‐β‐aryl)ethyl 2‐pyridyl thioethers via hydrothiolation α‐(trifluoromethyl)styrenes with pyridine‐2(1 H )‐thione was reported. The reaction proceeded smoothly regioselectively in an anti‐Markovnikov manner assistance DBU afforded a variety trifluoromethyl‐containing moderate to good yields.

Язык: Английский

Процитировано

Copper-Catalyzed Synthesis of 4-CF3-1,2,3-Triazoles: An Efficient and Facile Approach via Click Reaction DOI

Tinghong Tang,

C. Chen,

Xin Fu

и другие.

Molecules, Год журнала: 2024, Номер 29(6), С. 1191 - 1191

Опубликована: Март 7, 2024

Incorporation of a trifluoromethyl group with 1,2,3-triazoles motifs was described. We explored click reaction approach for regioselective synthesis 1-susbstituted-4-trifluoromethyl-1,2,3-triazoles in which 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) reacts commercial 2-bromo-3,3,3-trifluoropropene (BTP) to form 3,3,3-trifloropropyne (TFP) situ. Arising from merits associated the availability and stability BTP, high efficiencies CuI/1,10-Phenanthroline (Phen)-catalyzed cycloaddition reactions azides alkynes, this readily performed process takes place target yields, wide azide substrate scope. The potential value protocol demonstrated by its application gram-scale reaction.

Язык: Английский

Процитировано

Creation of a Chiral All-Carbon Quaternary Center Induced by CF₃ and CH₃ Substituents via Cu-Catalyzed Asymmetric Conjugate Addition DOI

Taiyo Yamamoto,

Masayuki Asakura,

Ken Yamanomoto

и другие.

Organic Letters, Год журнала: 2024, Номер 26(25), С. 5312 - 5317

Опубликована: Июнь 13, 2024

Cu-catalyzed asymmetric construction of a chiral quaternary center bearing CH3 and CF3 groups was achieved with high to excellent enantioselectivity using our originally developed ligands. The conjugate addition Me3Al β-CF3-substituted enones unsaturated ketoesters proceeded efficiently. use gives optically active furanones in yields enantioselectivities. perfluoroalkyl-substituted enone does not seem be favorable the present reaction.

Язык: Английский

Процитировано

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes to construct densely functionalized α-CF₃ tertiary alcohols DOI

Min-Ming Lu,

Ning Deng, Shiyu Li

и другие.

Green Chemistry, Год журнала: 2024, Номер 26(15), С. 8694 - 8700

Опубликована: Янв. 1, 2024

Visible-light-induced hydroxycarboxylation of α-trifluoromethylstyrenes under an air atmosphere was developed to construct densely functionalized α-CF 3 tertiary alcohols.

Язык: Английский

Процитировано

Iron-Mediated Dialkylation of Alkenylarenes with Benzyl Bromides DOI

Daniel M. Lux,

Daniel J. Lee, Rishi R. Sapkota

и другие.

The Journal of Organic Chemistry, Год журнала: 2024, Номер unknown

Опубликована: Апрель 4, 2024

We disclose a method for the dibenzylation of alkenylarenes with benzyl bromides using iron powder. This reaction generates branched alkyl scaffolds adorned functionalized aryl rings through formation two new C(sp3)–C(sp3) bonds at vicinal carbons alkenes. protocol tolerates electron-rich, electron-neutral, and electron-poor alkenylarenes. Mechanistic studies suggest benzylic radical intermediates as result single-electron transfer from iron, which is intercepted by

Язык: Английский

Процитировано

Facile Construction of Quaternary Carbon Centers via Dinuclear Titanium(III)‐Catalyzed Reductive Coupling of Tertiary Chlorides and Activated Olefins DOI

Wanjiao Chen,

Huaxi Sun,

Jie Jiang

и другие.

ChemCatChem, Год журнала: 2024, Номер 16(20)

Опубликована: Июнь 19, 2024

Abstract The establishment of all‐carbon quaternary carbon centers represents a pivotal aspect in the synthesis numerous natural products and pharmaceutical compounds, underscoring its paramount significance synthetic organic chemistry. Herein, we present novel strategy for generation through reductive coupling tertiary halides, catalyzed by dinuclear (salen)titanium catalysts. This catalytic framework demonstrates notable reactivity towards chlorides while maintaining inertness secondary primary chlorides, thereby facilitating exceptional chemoselectivity C−C bond formation. reaction proceeds with remarkable efficiency across diverse range substrates under mild conditions.

Язык: Английский

Процитировано

Decatungstate-Photocatalyzed Transformations of 2-Bromo-3,3,3-trifluoropropene for Selective Synthesis of Z/E-β-CF₃-Enones DOI

Xiao-Ya Yuan,

Zhimin Lü,

Xianqiang Huang

и другие.

Organic Letters, Год журнала: 2024, Номер unknown

Опубликована: Дек. 2, 2024

Condition-controlled switchable and divergent transformations of cost-effective 2-bromo-3,3,3-trifluoropropene (BTP) aldehydes were realized using a decatungstate (TBADT)-photocatalyzed strategy. The hydroacylated products, i.e., β,β-Br,CF

Язык: Английский

Процитировано