I₂-Mediated Site-Selective C–H Functionalization: Access to p-Amino-Substituted Unsymmetrical Benzils and Quinoxalines from Sulfoxonium Ylides

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(8), P. 5536 - 5545

Published: April 3, 2024

An I2-mediated approach for selective C–H functionalization of unprotected aniline derivatives synthesizing benzils and quinoxaline from sulfoxonium ylides has been described. Aniline ornamented with different functional groups showed good compatibility. They afforded the corresponding products moderate to high yields via a mild simple procedure. Finally, we validated practicality this method by scaling up reaction further conversion synthesized into other valuable molecules.

Language: Английский

---

Visible-Light-Induced C(sp³)-H Activation for Minisci Alkylation of Pyrimidines Using CHCl₃ as Radical Source and Oxidant

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 14, 2025

A highly efficient Minisci reaction of pyrimidines with alkyl radical generated from visible-light-induced activation simple C(sp3)-H feedstocks such as (cyclo)alkanes, ethers, alcohols, esters, and amides is reported. mechanistic study revealed that was via hydrogen atom transfer (HAT) dichloromethyl (·CHCl2), which by photoreduction chloroform.

Language: Английский

---

Annulative Coupling of Sulfoxonium Ylides with Aldehydes and Naphthols or Coumarins: Easy Access to Fused Dihydrofurans

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1645 - 1655

Published: Jan. 17, 2025

We present a novel, metal- and additive-free method for the robust synthesis of dihydrofuran-fused naphthalenes coumarins. This approach utilizes annulative coupling sulfoxonium ylides with aldehydes, naphthols, or coumarins at ambient temperature. The exhibits broad substrate compatibility, accommodating various functional groups on naphthol coumarin derivatives resulting in good to high yields desired products. Additionally, we successfully scaled up reactions, synthesized were further converted other valuable bioactive molecules, validating viability our approach.

Language: Английский

---

Three-component cyclization of 2-chloronitrobenzenes, sulfoxonium ylides, and elemental sulfur

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155574 - 155574

Published: April 1, 2025

Language: Английский

---

Annulation of 2-Aroyl D–A Cyclopropanes via Selectively Ring-Opening Process with o-Benzenediamines to Access Quinoxaline Derivatives

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10333 - 10337

Published: July 2, 2024

An annulation reaction of 2-aroyl D-A cyclopropanes with

Language: Английский

---

Reactivities and mechanisms in organic reactions involving activation of elemental sulfur under basic conditions

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: 11, P. 100086 - 100086

Published: July 27, 2024

As a readily available and benign waste product of the petrochemical industry, elemental sulfur displays desirable characteristics as raw material for new processes. Accordingly, use reactant or reagent in synthetic organic chemistry receives continuous interest. The implementation procedures often necessitates presence basic nucleophilic compounds, which are known to serve activators, enabling diverse range transformations. However, underlying mechanisms still poorly understood, even synthetically useful well-established reactions that have been decades. While numerous reviews focus on various types products accessible via involving sulfur, this manuscript will put its emphasis common mechanistic steps these transformations, highlighting discussing studies postulated pathways.

Language: Английский

---

Lithium Bromide-Promoted Formal C(sp³)–H Bond Insertion Reactions of β-Carbonyl Esters with Sulfoxonium Ylides to Synthesize 1,4-Dicarbonyl Compounds

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(10), P. 6974 - 6986

Published: May 4, 2024

A LiBr-promoted formal C(sp3)–H bond insertion reaction between β-carbonyl esters and sulfoxonium ylides is established. This practical has a wide range of substrate scope for both to give variety 1,4-dicarbonyl compounds with 43–94% yields. The features transition-metal-free conditions exclusive C-alkylation chemselectivity. use bench-stable overcomes previous methods that require transition metal as catalysts unstable diazo or toxic haloketones alkylation reagents.

Language: Английский

---

Annulative coupling of α-substituted acrylic acids and sulfoxonium ylides: Easy access to bioactive γ-butyrolactones

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(67), P. 8872 - 8875

Published: Jan. 1, 2024

We present a straightforward, catalyst- and additive-free method for synthesizing keto γ-butyrolactones using readily available β-keto sulfoxonium ylides acrylic acids. This robust approach demonstrates exceptional compatibility with various functional groups on α-substituted acids, resulting in good to high yields of the anticipated products. Moreover, practicality this was validated through large-scale reactions successful conversion some synthesized derivatives into bioactive natural products, including L-factor, muricatacin, cytosporanone A.

Language: Английский

---

Pragmatic Access to Hybrid Quinoxaline Scaffold Mediated by Elemental Sulfur Enabling Actualization to π-Extended and Aza-Annulated Heterocyclic Units

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Sept. 27, 2024

A metal-free approach for synthesizing hybrid quinoxaline derivatives from sulfoxonium ylide and a 1,5-bis-nucleophilic N-heterocycle mediated by elemental sulfur is presented to illuminate the [5+1] cascade cyclization sequence. Large-scale synthesis postsynthetic functionalizations annulative π-extension intramolecular aza-annulation reactions reveal potential utility actualize fabricated approach.

Language: Английский

---

Annulative coupling of sulfoxonium ylides with 2‑amino(thio)phenols: Easy access to 2-acyl benzox(thio)azoles

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

A novel elemental sulfur-mediated approach for the synthesis of 2-acyl benzothiazoles and benzoxazole derivatives via annulative coupling sulfoxonium ylides with 2-aminobenzenethiol 2-aminophenol derivatives, respectively, is described.

Language: Английский

---