Sustainable and scalable one-pot synthesis of diaryliodonium salts

Chemical Communications, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Two one-pot syntheses of diaryliodonium triflates are presented, rendering the production these electrophilic arylating agents more sustainable.

Language: Английский

---

Arylation of Diethyl Acetamidomalonate with Diaryliodonium Salts En Route to α-Arylglycines

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 9923 - 9928

Published: July 1, 2024

Diethyl acetamidomalonate (DEAM) has been widely used for the synthesis of α-amino acids via C-alkylation under basic conditions followed by hydrolysis/decarboxylation. In contrast, C-arylation this reagent remains undeveloped. Herein, we report a novel strategy racemic α-arylglycines based on selective arylation DEAM with diaryliodonium salts mild, transition metal-free conditions. The reaction features good functional group tolerance and easy scalability is applicable to chemoselective C-H-modification arenes including approved drugs, thus enabling straightforward approach complex that would be challenging make otherwise.

Language: Английский

---

Synthesis of Diaryl Ethers via Hypervalent Iodine-Mediated C–H Functionalization

Organic Letters, Journal Year: 2024, Volume and Issue: 26(37), P. 7864 - 7868

Published: Sept. 9, 2024

A hypervalent iodine-reagent-based C-H functionalization strategy was utilized to synthesize diaryl ethers. This method directly transforms various arenes into their corresponding diaryliodonium salts, followed by a C-O coupling reaction produce structurally diverse The efficacy of this approach in the late-stage structural modifications complex molecules demonstrated.

Language: Английский

---

Iodonium(III) Ylide: An Iodoalkylation Reagent with Aryne

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

Published: Feb. 5, 2025

A tandem Hexadehydro-Diels–Alder (HDDA)/[2 + 2] cycloaddition/aryl migration reaction of iodonium ylide with tetrayne is described, in which served as a unique double bond and reacted aryne to form four-membered iodonium(III) cycle, then converted iodoarene after aryl group from iodine adjacent carbon. This strategy allows the efficient construction fully substituted compounds.

Language: Английский

---

Synthesis of 1,2-Disubstituted-3-thioindoles by the Madelung Reaction

Russian Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 61(2), P. 217 - 224

Published: Feb. 1, 2025

Language: Английский

---

Hypervalent Iodine-Mediated Selective Monofunctionalization of Calix[4]arenes

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

Published: April 30, 2025

The selective introduction of a single functionality on the upper rim calix[4]arene is challenging due to identical reactivity its four aryl units. In this study, we introduce novel strategy for monofunctional modification calix[4]arenes using hypervalent iodine-mediated C-H functionalization. This process yields calix[4]arene-iodonium salt, which can be easily isolated distinct solubility compared native calixarene. versatile intermediate efficiently undergoes C-O, C-N, and C-S couplings with variety nucleophiles, including amines, phenols, thiols, sulfinate salts under mild conditions. enables streamlined structural diversification calix[4]arenes, opening new avenues design supramolecular macrocycles tailored functions.

Language: Английский

---

Site-Selective Nitration of Arene via Hypervalent Iodine-Mediated C–H Functionalization

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

Published: May 7, 2025

We developed a novel nitration method using hypervalent iodine for site-selective C-H functionalization. This technique efficiently synthesizes nitroarenes with high regioselectivity and is scalable, enhancing the late-stage modification of bioactive pharmaceuticals.

Language: Английский

---

Interrupted Plancher Rearrangement Initiated by Dearomative Epoxide–Indole Cyclization: Formal Umpolung Reactivity of Indoles

Organic Letters, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 12, 2024

We herein report the serendipitous discovery of interrupted Plancher rearrangement initiated by an HFIP-promoted dearomative epoxide-indole cyclization, unlocking a new blueprint to formal C3 umpolung reactivity indoles. This rapid complexity generating cascade process paves way toward class fused-bridged indolines in high yields and under full regio- diastereocontrol. The reaction is amenable wide range substituents starting materials.

Language: Английский

---

Copper-Catalyzed Cascade Cyclization of 2-Nitrochalcones with NH-Heterocycles

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

Published: Nov. 19, 2024

We developed a method for allowing cascade cyclization of 2-nitrochalcones with pyrazoles, imidazole, and indazole in the presence CuI catalyst, DBU base, THF solvent. The conditions were tolerant an array useful functionalities including ester, nitro, cyano, halogen groups. A mechanistic consideration was also provided, as H2O2 presumably byproduct. Our appears to be rare example directly prepare C3-heterocyclic unprotected indoles.

Language: Английский

---