Copper-Catalyzed Asymmetric Defluoroborylation of 1-(Trifluoromethyl)Alkenes

Chem, Год журнала: 2018, Номер 4(9), С. 2201 - 2211

Опубликована: Июль 26, 2018

Язык: Английский

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Plausible Rh(V) Intermediates in Catalytic C–H Activation Reactions

ACS Catalysis, Год журнала: 2017, Номер 8(1), С. 242 - 257

Опубликована: Ноя. 20, 2017

Catalysis by defined transition-metal complexes has captivated the attention of scientific community over last decades. The well-documented utility Rh(III) in C–H activation reactions have enabled development a plethora new catalytic methods. High-valent species were first predicted palladium-based transformations. From those early studies, it was apparent that differences reactivity and selectivity could be expected. By analogy, higher valent Rh(V) represent approach offer different opportunities to improve broaden current state-of-the-art field.

Язык: Английский

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Nickel-Catalyzed Enantioselective Reductive Aryl Fluoroalkenylation of Alkenes

ACS Catalysis, Год журнала: 2019, Номер 9(10), С. 9127 - 9133

Опубликована: Сен. 4, 2019

Enantioselective Ni-catalyzed reductive aryl monofluoroalkenylation of alkenes between bromides and gem-difluoroalkenes has been developed. The reaction proceeding under room temperature base-free conditions tolerates a wide range functional groups on both coupling partners. Various synthetically useful oxindoles containing monofluoroalkenyl substituent are obtained in good yields with 85%–95% enantiomeric excess. In addition, the synthetic method can be further applied to late-stage complex biologically active compounds.

Язык: Английский

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Synthesis of Monofluoroalkenes: A Leap Forward

Synthesis, Год журнала: 2018, Номер 50(05), С. 881 - 955

Опубликована: Янв. 11, 2018

Monofluoroalkenes have found wide application in organic chemistry, medicinal and materials science. This review summarizes the most recent advances made regarding preparation of monofluoroalkenes, covering period between October 2010 September 2017. is divided three main parts, one for each possible substitution pattern, namely di-, tri-, tetrasubstituted. Then, class, further subclassification according to reaction type. 1 Introduction 2 Disubstituted 2.1 α-Monofluoroalkenes 2.2 β-Monofluoroalkenes 3 Trisubstituted 4 Tetrasubstituted 5 Conclusions

Язык: Английский

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Recent Advances in Transition Metal‐Catalyzed Functionalization of gem‐Difluoroalkenes

Israel Journal of Chemistry, Год журнала: 2020, Номер 60(3-4), С. 313 - 339

Опубликована: Март 1, 2020

gem-Difluorinated alkenes are readily accessible building blocks that can undergo functionalization to provide a broad spectrum of fluorinated and non-fluorinated products. Herein, we review recent (since 2017) transition metal-catalyzed transformations these specialized summarize general reactivity patterns reactions. Many reactions net C-F bond deliver monofluorinated These typically proceed through β-fluoro alkylmetal intermediates eliminate β-fluoride monofluoroalkene A second series exploit coinage metal fluorides add F- the gem-difluorinated alkene, further delivers trifluoromethyl-containing In stark contrast, few in "fluorine-retentive processes" difluoromethylene-based

Язык: Английский

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Recent advances in three-component difunctionalization ofgem-difluoroalkenes

Chemical Communications, Год журнала: 2020, Номер 56(72), С. 10442 - 10452

Опубликована: Янв. 1, 2020

Three-component difunctionalization ofgem-difluoroalkenesviathe generation and transformation of a α-fluoroalkylated carbanion, carbon–metal species, radical, carbocation intermediate.

Язык: Английский

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Copper‐Catalyzed Stereoselective Defluorinative Borylation and Silylation of gem‐Difluoroalkenes

Advanced Synthesis & Catalysis, Год журнала: 2017, Номер 360(5), С. 1032 - 1037

Опубликована: Дек. 27, 2017

Abstract The copper‐catalyzed stereoselective defluorinative borylation and silylation of gem ‐difluoroalkenes was developed. protocol led to the exclusive formation Z type monofluoroalkenyl borons silanes in generally good efficiency with broad substrate scope. products formed could be readily transformed other F‐containing molecules by taking advantage versatile reactivities C−B C−Si bonds. Experimental theoretical mechanistic studies were conducted which support an olefin insertion/ syn ‐planar β‐F elimination pathway. magnified image

Язык: Английский

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Access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety via a double decarboxylative formal ring-expansion process under palladium catalysis

Chemical Science, Год журнала: 2018, Номер 9(13), С. 3276 - 3281

Опубликована: Янв. 1, 2018

Direct access to benzo-fused nine-membered heterocyclic alkenes with a trifluoromethyl carbinol moiety was achieved via palladium-catalysis.

Язык: Английский

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Highly tunable multi-borylation of gem-difluoroalkenes via copper catalysis

Nature Catalysis, Год журнала: 2018, Номер 1(11), С. 860 - 869

Опубликована: Окт. 26, 2018

Язык: Английский

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Mild Cobalt(III)‐Catalyzed Allylative C−F/C−H Functionalizations at Room Temperature

Chemistry - A European Journal, Год журнала: 2017, Номер 23(50), С. 12145 - 12148

Опубликована: Июль 4, 2017

Sustainable, cobalt-catalyst enabled, synthetically significant C-F/C-H functionalizations were achieved with an ample substrate scope at ambient temperature of 25 °C, thereby delivering perfluoroallylated heteroarenes. Detailed experimental and computational mechanistic studies on the provided strong support for a facile C-F cleavage.

Язык: Английский

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