Chemical Science, Journal Year: 2021, Volume and Issue: 12(46), P. 15399 - 15406
Published: Jan. 1, 2021
Simple, modular assembly of complex fluoroalkyl-containing oxindole derivatives with a broad scope and excellent functional group tolerance under mild conditions (metal- photocatalyst-free). Benzyl iodides were identified as key intermediates.
Language: Английский
Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: unknown
Published: Jan. 1, 2024
This study describes a pioneering visible-light-induced phosphine-catalyzed halogen-atom transfer (XAT) strategy that heralds new era in the difunctionalization of [1.1.1]propellane.
Language: Английский
Citations
12
The Journal of Organic Chemistry, Journal Year: 2019, Volume and Issue: 85(2), P. 942 - 951
Published: Dec. 19, 2019
A visible light-promoted difluoroalkylation reaction of arenes or heterocycles, using triaryl phosphine as the catalyst and difluoroalkyl iodide alkylating agent, is presented. The strategy highlighted by photocatalyst-free, mild conditions a broad substrate scope. Mechanistic experiments indicate that this involves radical-chain process initiated an electron donor–acceptor complex formed from phosphine.
Language: Английский
Citations
68
Organic Chemistry Frontiers, Journal Year: 2020, Volume and Issue: 7(16), P. 2349 - 2371
Published: Jan. 1, 2020
The background and recent breakthroughs in the single-electron-transfer (SET) reactions with trivalent tertiary phosphines are summarized discussed detail, an outlook developments within this field is provided.
Language: Английский
Citations
68
Chemical Communications, Journal Year: 2020, Volume and Issue: 56(26), P. 3801 - 3804
Published: Jan. 1, 2020
A new general de novo synthesis of pharmaceutically important α-aryl β-perfluoroalkyl ketones has been disclosed. Compared with trifluoromethylation-initiated radical 1,2-aryl migration α,α-diaryl allylic alcohols, this protocol employs a strategy biomimetic carbene catalysis to assemble alkene, aldehyde and perfluoroalkyl reagents, providing access products excellent flexibility the aryl unit group. This method also demonstrates functional group compatibility, including some Grignard reagent sensitive groups.
Language: Английский
Citations
64
Synthesis, Journal Year: 2022, Volume and Issue: 54(08), P. 1919 - 1938
Published: Feb. 21, 2022
Abstract Perfluoroalkylation is one of the most important methods for introduction multiple fluorine atoms into organic molecules in a single step. The use photoinduced technology common strategy that uses outstanding oxidation or reduction ability photoredox catalyst its excited state to generate perfluoroalkyl radicals from halides. thus obtained can undergo various subsequent reactions under mild conditions, such as ATRA reaction alkenes, alkynes, and 1,n-enynes; carbo/heteroperfluoroalkylation alkenes isocyanides; C–H/F perfluoroalkylation. This allows expedient incorporation groups molecular motifs. Perfluorinated functional are still demand pharmaceutical material sciences; this short review discusses recent advances perfluoroalkylation methodologies technologies. 1 Introduction 2 Photocatalytic Alkenes, Alkynes, 1,n- Enynes 3 Carboperfluoroalkylation Heteroperfluoroalkylation Isocyanides, Hydrazones 4 ATRE Reactions Alkenes with Perfluoroalkyl Halides 5 C–X (X = H, F) Bond 6 Continuous Flow Strategies 7 Conclusions
Language: Английский
Citations
38
Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(30)
Published: May 20, 2022
Abstract A novel distal radical rearrangement of alkoxyphosphine is developed for the first time and applied to regioselective fluoroalkylphosphorylation unactivated olefins. By employing a one‐pot two‐step reaction (bis)homoallylic alcohols, organophosphine chlorides, fluoroalkyl iodides under CFL (compact fluorescence light) irradiation, series fluoroalkylphosphorylated alkyl alcohols are easily synthesized by regiospecific installing phosphonyl onto inner carbon terminal olefins further iodination/hydroxylation. Mechanism studies reveal that migration undergoes distinctive cyclization/β‐scission on lone electron pair phosphorus, resulting in C−P bond formation C−O cleavage.
Language: Английский
Citations
29
The Journal of Organic Chemistry, Journal Year: 2020, Volume and Issue: 85(16), P. 10574 - 10583
Published: July 15, 2020
Although organic-based photocatalysts provide an inexpensive, environmentally friendly alternative, many are incapable of absorption within the visible wavelength range; this ultimately influences their effectiveness. Photocatalytic reactions usually proceed via single electron transfer (SET) or energy (ET) processes from photoexcited molecules to various substrates. In our study, carbohalogenation olefins was accomplished by combining CBr4 and 4-Ph-pyridine under irradiation. The atom radical addition reaction catalyzed in situ-formed photocatalyst halogen bonding afford a variety products moderate good yields. Essential is formation CT complex with haloalkene, which triggers charge separation and, ultimately, leads C-centered radical. While taking advantage relatively readily available, reagents, indirect activation substrate catalyst paves way for more efficient routes, especially otherwise challenging chemical syntheses.
Language: Английский
Citations
50
Chemical Communications, Journal Year: 2020, Volume and Issue: 56(66), P. 9453 - 9456
Published: Jan. 1, 2020
A visible-light-promoted fluoroalkylation-thiolation of alkenes is described.
Language: Английский
Citations
48
Organic & Biomolecular Chemistry, Journal Year: 2020, Volume and Issue: 18(41), P. 8278 - 8293
Published: Jan. 1, 2020
Radical vicinal carbohalofunctionalization of C-C multiple bonds via atom transfer processes constitutes an efficient method for the construction halogenated building blocks with complete economy radical cleavage a pre-existing carbon-halogen σ-bond reagent and their transposition over π-bond alkenes alkynes. This review summarizes recent advances in photo-induced version this class transformations. A variety transition-metal complexes, organic dyes, phosphines, amines, phenols aldehydes were utilized as catalysts existing bond corresponding presence light source. Alongside 1,2-haloalkylation haloperfluoroalkylation reactions, addition (ATRA) or cyclization (ATRC) reactions aryl halides are also discussed.
Language: Английский
Citations
45
Advanced Synthesis & Catalysis, Journal Year: 2020, Volume and Issue: 363(4), P. 924 - 936
Published: Dec. 24, 2020
Abstract The photochemistry of organophosphorus compounds and their reactions with carbon‐centred radicals was studied from the 1950s to 70s, but has not been well exploited in synthetic chemistry until very recently. This review discusses various modes reactivity that phosphorus display radical C−C bond forming reactions, including role phosphonium salts as precursors, phosphines phosphites deoxygenating agents oxygen‐centred electron‐ charge‐transfer chemistry. We also highlight potential these processes have future development new cascade processes. magnified image
Language: Английский
Citations
43