Visible-Light-Induced Nickel-Catalyzed Radical Cross-Couplings to Access α-Aryl-α-trifluoromethyl Alcohols

Organic Letters, Год журнала: 2022, Номер 24(50), С. 9332 - 9336

Опубликована: Дек. 9, 2022

A photochemically induced nickel-catalyzed radical cross-coupling of phthalimido trifluoroethanol with aryl bromides to furnish α-aryl-α-trifluoromethyl alcohols is reported. This reaction proceeds via a photoinduced charge transfer an electron donor-acceptor complex between Hantzsch ester and trifluoroethanol, followed by 1,2-hydrogen atom transfer, generate the α-hydroxytrifluoroethyl for bromides. No exogenous photocatalysts or stoichiometric metal reductants are required in this mild operationally simple protocol. Broad substrate compatibility excellent functional group tolerance observed.

Язык: Английский

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Electrochemical Reductive Functionalization of Alkenes with Deuterochloroform as a One-Carbon Deuteration Block

Organic Letters, Год журнала: 2022, Номер 24(47), С. 8645 - 8650

Опубликована: Ноя. 16, 2022

Deuterochloroform is the most common organic deuterated solvent. However, synthetic chemistry of deuterochloroform has been marginally explored because its intrinsic limitations, including elimination and scrambling. In this work, an electrochemical protocol was developed to use as a one-carbon deuteration block in cyclopropanation hydrochloromethylation alkenes. By employing different reaction conditions, chemoselectivity could be regulated give divergent products. Typically, deuterium incorporation above 93% 99% achieved.

Язык: Английский

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Iron-catalysed reductive coupling for the synthesis of polyfluorinated compounds

Chemical Communications, Год журнала: 2022, Номер 58(100), С. 13915 - 13918

Опубликована: Янв. 1, 2022

Herein we reported the use of Earth-abundant iron as catalytic metal in presence Mn to induce difluorobromoacetates form carbon radicals, which reacted with trifluoromethyl olefins followed by β-F elimination generate corresponding gem-difluoroolefins. The cross-electrophile coupling displayed excellent functional group tolerance and broad substrate scope under mild reductive conditions, affording a large number polyfluorinated compounds, could be further transformed other valuable molecules.

Язык: Английский

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Catalytic Asymmetric Construction of CF3-Substituted Chiral sp3 Carbon Centers

Synthesis, Год журнала: 2022, Номер 54(17), С. 3708 - 3718

Опубликована: Апрель 25, 2022

Abstract Due to the unique steric and electronic nature of fluorine atom, organofluorine compounds have received significant attention in fields pharmaceuticals agrochemicals. In particular, CF3 group is frequently found biologically active compounds. However, compared aryl- alkenyl-CF3-containing molecules, construction sp3 carbon-based alkyl-CF3-containing particularly via catalytic enantioselective synthesis, remains a considerable challenge spite their high potential medicinal applications. This short review focuses on recent advances this research area, reported strategies are categorized according reaction types starting substrates. addition, chiral catalysts, substrate scope, mechanisms briefly summarized. 1 Introduction 2 Stereoselective Group 2.1 Nucleophilic Addition Carbonyls Imines 2.2 Electrophilic Substitution at α Position 2.3 Allylic 3 Functionalization CF3-Substituted Molecules 3.1 α-CF3 3.2 α-Halo Compounds 3.3 Addition-Type Reactions with Alkenes 4 Conclusion Outlook

Язык: Английский

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Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene

Chemical Science, Год журнала: 2022, Номер 13(23), С. 6959 - 6966

Опубликована: Янв. 1, 2022

Herein, we present a facile and efficient allylation method via Ni-catalyzed cross-electrophile coupling of readily available allylic acetates with variety substituted alkenyl bromides using zinc as the terminal reductant.

Язык: Английский

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