The Application of Sulfonyl Hydrazides in Electrosynthesis: A Review of Recent Studies

ACS Omega, Journal Year: 2022, Volume and Issue: 7(44), P. 39531 - 39561

Published: Oct. 27, 2022

Sulfonyl hydrazides are viewed as alternatives to sulfinic acids and their salts or sulfonyl halides, which broadly used in organic synthesis work active pharmaceutical substances. Generally, considered good building blocks show powerful value a diverse range of reactions construct C–S bonds C–C bonds, even C–N sulfur, carbon, nitrogen sources, respectively. As profound synthetic tool, the electrosynthesis method was recently achieve efficient green applications hydrazides. Interestingly, many unique novel electrochemical syntheses using radical precursors have been developed, including cascade reactions, functionalization heterocycles, well continuous flow combining with since 2017. Accordingly, it is necessary specifically summarize recent developments only more deeply understand better design reactions. Herein, research 2017 reviewed detail based on chemical structures products reaction mechanisms.

Language: Английский

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Decarboxylative C–H silylation of N-heteroarenes with silanecarboxylic acids

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(17), P. 2449 - 2452

Published: Jan. 1, 2023

Established decarboxylative Minisci reactions are limited to aliphatic carboxylic acids, as their analogs, silanecarboxylic have been rarely investigated. Herein, we present a new Minisci-type reaction of N-heteroarenes with acids under photo- or silver-mediated conditions. This C-H silylation strategy provides efficient access diverse N-heteroarylsilanes in moderate excellent yields high regioselectivity, among which Ag-catalysed decarboxylation furnishes an unprecedented method for silyl radical generation.

Language: Английский

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Silylation and (Hetero)aryl/alkenylation of Unactivated Alkenes via Radical-Mediated Distal 1,4-Migration with Hydrosilanes under Organophotocatalysis

Organic Letters, Journal Year: 2024, Volume and Issue: 26(21), P. 4526 - 4531

Published: May 18, 2024

We report a novel organic photoredox catalysis to achieve unprecedented γ-(hetero)aryl/alkenyl-δ-silyl aliphatic amines via silyl-mediated distal (hetero)aryl/alkenyl migration of aromatic/alkenyl bearing unactivated alkenes with hydrosilanes. This protocol features mild and metal-free reaction conditions, high atom economy, excellent selectivity, functional group compatibility. Mechanistic studies suggest that silylation (hetero)aryl/alkenylation involve hydrogen transfer subsequent 1,4-migration remote from nitrogen carbon.

Language: Английский

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Visible-light-driven PhSSPh-catalysed regioselective hydroborylation of α,β-unsaturated carbonyl compounds with NHC-boranes

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(60), P. 8380 - 8383

Published: Jan. 1, 2022

A photo-induced transition-metal-free regioselective hydroborylation of α,β-unsaturated carbonyl compounds is developed. The PhSSPh reagent was employed as the photocatalyst, and NHC-BH3 used boron source. This transformation shows a broad substrate scope provides wide range α-borylcarbonyl molecules in good to excellent yields.

Language: Английский

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“On-water” defluorophosphorylation of trifluoromethylated enones with phosphine oxides

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(16), P. 6489 - 6497

Published: Jan. 1, 2023

An efficient “on-water” reaction of β-trifluoromethylated enones with phosphine oxides was developed for the preparation phosphorylated gem -difluorodienes excellent Z -selectivity.

Language: Английский

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Visible-light-driven selective difluoroalkylation of α-CF₃ alkenes to access CF₂-containing gem-difluoroalkenes and trifluoromethylalkanes

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(2), P. 458 - 465

Published: Nov. 23, 2023

A visible-light-mediated selective difluoroalkylation of α-trifluoromethyl alkenes with difluoroalkylating reagents was developed. This protocol allowed the formation gem -difluoroalkene difluoroacetates and trifluoromethylated difluoroacetamides.

Language: Английский

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Photocatalyzed 1,3-Bromodifluoroallylation of [1.1.1]Propellane with α-Trifluoromethylalkenes and KBr Salts

Organic Letters, Journal Year: 2024, Volume and Issue: 26(32), P. 6889 - 6893

Published: Aug. 6, 2024

Herein we unveil a visible-light-driven transition-metal-free 1,3-bromodifluoroallylation of [1.1.1]propellane. This reactivity is harnessed through organophotocatalysis, providing practical synthetic pathways to 1-brominated-3-

Language: Английский

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Photoredox/nickel cooperatively catalyzed radical allylic silylation of allyl acetates – Scope and mechanism

Journal of Catalysis, Journal Year: 2023, Volume and Issue: 418, P. 312 - 319

Published: Jan. 28, 2023

Language: Английский

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Photocatalytic synthesis of alkyl–alkyl sulfonesviadirect C(sp³)–H bond functionalization

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(13), P. 2822 - 2827

Published: Jan. 1, 2023

We report a highly efficient one-pot, three-component strategy for the construction of alkyl-alkyl sulfones through photoinduced TBADT-catalyzed C(sp3)-H sulfonylation unactivated hydrocarbon compounds. A wide range commercially available compounds and bioactive molecules can be successfully applied to catalytic system, affording corresponding in good excellent yields (>50 examples, up 87% yield).

Language: Английский

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Visible-light-induced decarboxylation/defluorosilylation protocol for synthesis ofgem-difluoroalkenes

Catalysis Science & Technology, Journal Year: 2023, Volume and Issue: 13(6), P. 1628 - 1632

Published: Jan. 1, 2023

A catalytic defluorosilylation is disclosed that provides a concise route to gem -difluoroallylsilanes with broad functional-group compatibility from trifluoromethylalkenes and silacarboxylic acids, stable silyl radical precursors.

Language: Английский

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