Aromatic halogenation using carborane catalyst

Chem, Journal Year: 2023, Volume and Issue: 10(1), P. 402 - 413

Published: Nov. 6, 2023

Language: Английский

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α-Bromoacetate as a Mild and Safe Brominating Agent in the Light-Driven Vicinal Dibromination of Unactivated Alkenes and Alkynes

Organic Letters, Journal Year: 2024, Volume and Issue: 26(26), P. 5478 - 5481

Published: June 25, 2024

Light-induced vicinal dibromination of unactivated alkenes and alkynes has been demonstrated by using methyl α-bromoacetate as a mild brominating agent. A near-visible light (370 nm) light-emitting diode (LED) mediates this simple reaction under conditions with the inexpensive nontoxic α-bromoacetate. The proceeds well both terminal internal those contained in N/O-heterocycles, indicating its versatility synthesizing dibrominated organic compounds.

Language: Английский

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Merging Iron-Mediated Radical Ligand Transfer (RLT) Catalysis and Mechanochemistry for Facile Dihalogenation of Alkenes

ACS Catalysis, Journal Year: 2024, Volume and Issue: unknown, P. 13747 - 13758

Published: Aug. 30, 2024

With the growing emphasis on cost- and atom-economical chemical synthesis, mechanochemistry has attracted considerable attention for providing environmentally friendly alternatives to traditional solvent-based organic transformations. Herein, we demonstrate use of facilitate alkene dihalogenation via iron-mediated radical ligand transfer (RLT) catalysis, producing diverse vicinal dichloro, dibromo, bromochloro molecules. The method is characterized by its simplicity, rapid reaction time, high chemo- regioselectivity, broad functional group tolerance, accommodating both activated unactivated alkenes alkynes. Mechanistic insights suggest nature these processes, underscoring effectiveness mechanochemically driven RLT catalysis modular functionalization unsaturated hydrocarbons.

Language: Английский

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Synthesis of gem-Diborylcyclopropyl Ketones via Conjugate Addition of Chlorodiborylmethane to α,β-Unsaturated Ketones

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 3, 2025

The carbanion derived from chlorodiborylmethane can act as a soft nucleophile, while the halogen substituent subsequently function leaving group. Taking advantage of this feature, we herein have developed an efficient synthesis gem-diborylcyclopropyl ketones diverse range enone substrates. We also demonstrated synthetic utility protocol by leveraging highly transformable nature cyclopropyl moiety and C-B bonds.

Language: Английский

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DBDMH-Promoted Methylthiolation in DMSO: A Metal-Free Protocol to Methyl Sulfur Compounds with Multifunctional Groups

Molecules, Journal Year: 2023, Volume and Issue: 28(15), P. 5635 - 5635

Published: July 25, 2023

Organic thioethers play an important role in the discovery of drugs and natural products. However, green synthesis organic sulfide compounds remains a challenging task. The convenient efficient 5-alkoxy-3-halo-4-methylthio-2(5H)-furanones from DMSO is performed via mediation 1,3-dibromo-5,5-dimethylhydantoin (DBDMH), affording facile route for sulfur-functionalization 3,4-dihalo-2(5H)-furanones under transition metal-free conditions. This new approach has demonstrated functionalization non-aromatic Csp2-X-type halides with unique structures containing C-X, C-O, C=O C=C bonds. Compared traditional methods using metal catalysts ligands, this reaction many advantages, such as lower temperature, shorter time, wide substrate range good functional group tolerance. Notably, plays multiple roles, simultaneously used odorless methylthiolating reagent safe solvent.

Language: Английский

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α-Bromoacetate as a Mild and Safe Brominating Agent in the Light-Driven Vicinal Dibromination of Unactivated Alkene and Alkynes

Published: May 14, 2024

Light-induced vicinal dibromination of unactivated alkenes and alkyne has been demonstrated by using methyl alpha-bromoacetate as a mild brominating agent. Near-visible light (370 nm) light-emitting diode (LED) mediates this simple reaction under conditions with the inexpensive non-toxic -bromoacetate. The proceeds well both terminal internal alkynes, those contained in natural products N/O-heterocycles, indicating its versatility synthesizing dibrominated organic compounds.

Language: Английский

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Bromination of indazoles enhanced by organic-dye, visible-light photoredox catalysis

Tetrahedron, Journal Year: 2023, Volume and Issue: 142, P. 133523 - 133523

Published: June 17, 2023

Language: Английский

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Thiophane‐Catalyzed Umpolung of N‐Bromoimides for Dibromination of Olefins

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(13)

Published: Feb. 21, 2024

Abstract A thiophane‐catalyzed dibromination of olefins using NBS as the sole bromine source has been developed, providing a low‐cost and mild methodology for preparing vicinally dibrominated compounds from electron‐neutral or ‐deficient alkenes. The mechanistic investigation showed that 2,3‐dihydrothiophene generated in situ reaction thiophane with was actual catalyst, which reversed polarity to yield bromide ion.

Language: Английский

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Ultrasound-promoted three-component halogenation-azaheteroarylation of alkenes involving carbon-halogen and carbon-carbon bond formation

Tetrahedron Letters, Journal Year: 2022, Volume and Issue: 110, P. 154198 - 154198

Published: Oct. 13, 2022

Language: Английский

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Direct bromoalkoxylation of enones under acid-free conditions

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 126, P. 154647 - 154647

Published: July 17, 2023

Language: Английский

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