Advancement of vinylene carbonate as a coupling partner in metal-catalyzed C–H functionalization

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5717 - 5734

Published: Jan. 1, 2023

Vinylene carbonate (VC) has emerged as a promising coupling partner to participate in various attractive C–H conversions and implement an increasing number of novel reactions. In this review, we provide summary the advancements achieved metal-catalyzed functionalization using VC.

Language: Английский

---

Rhodium‐Catalyzed Direct Vinylene Annulation of Sulfoxonium Ylides and N‐carbamoylindoles with Vinylene Carbonate

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(9), P. 1457 - 1464

Published: April 14, 2023

Abstract In this study, Rh(III)‐catalyzed C−H bifunctionalization and direct vinylene annulation of sulfoxonium ylides N ‐carbamoylindoles with carbonate was accomplished, which afforded a series naphthalenones containing β‐ketosulfoxonium ylide moiety, isocoumarins, pyrimidones. This protocol featured mild conditions, broad substrate scope, functional‐groups compatibility. addition, related applications preliminary mechanistic exploratory were also investigated magnified image

Language: Английский

---

Rh(III)-Catalyzed C–H Functionalization/Annulation of 1-Arylindazolones: Divergent Synthesis of Fused Indazolones and Allyl Indazolones

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(6), P. 3499 - 3508

Published: March 9, 2023

Rh(III)-catalyzed C-H/N-H annulation and C-H allylation of phenylindazolones have been realized by employing 5-methylene-1,3-dioxan-2-one 4-vinyl-1,3-dioxolan-2-one as scalable cross-coupling partners, delivering functionalized indazolone fused heterocycles branched linear allyl indazolones respectively in moderate to high yield. These divergent synthesis protocols showcase mild conditions, broad substrate scope, functional-group compatibility. In addition, scale-up preliminary mechanistic exploratory were also accomplished.

Language: Английский

---

Innovative advancements in transition metal-catalyzed C(sp)-H bond activation of phthalazinone: Unlocking the gateway to diverse hybrid polyheterocyclic architectures

Tetrahedron Letters, Journal Year: 2025, Volume and Issue: unknown, P. 155618 - 155618

Published: April 1, 2025

Language: Английский

---

Rhodium-catalyzed annulation of hydrazines with vinylene carbonate to synthesize unsubstituted 1-aminoindole derivatives

RSC Advances, Journal Year: 2024, Volume and Issue: 14(7), P. 4804 - 4809

Published: Jan. 1, 2024

The step-economical synthesis of C2, C3-unsubstituted 1-aminoindole derivatives through rhodium-catalyzed annulation hydrazines with vinylene carbonate.

Language: Английский

---

Rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinones with vinylene carbonate

Chemical Communications, Journal Year: 2023, Volume and Issue: 59(98), P. 14559 - 14562

Published: Jan. 1, 2023

A novel organic transformation involving rhodium-catalyzed divergent dehydroxylation/alkenylation of hydroxyisoindolinone with vinylene carbonate is reported, and the promising reagent presents a distinct chemical reactivity as vinyl-oxygen cyclic synthon.

Language: Английский

---

Rhodium-catalyzed C–H carboxymethylation of anilines with vinylene carbonate

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(41), P. 8320 - 8328

Published: Jan. 1, 2023

A rhodium-catalyzed synthesis of phenylacetate has been realized by direct C-H carboxymethylation anilines bearing removable directing groups. The reaction occurred most efficiently in air, without any external base or oxidant. This methodology is expected to provide a facile and general access various bioactive 2-amino aromatic acetic acid derivatives.

Language: Английский

---

Base-Catalyzed Nucleophilic Addition Reaction of Indoles with Vinylene Carbonate: An Approach to Synthesize 4-Indolyl-1,3-dioxolanones

Molecules, Journal Year: 2023, Volume and Issue: 28(21), P. 7450 - 7450

Published: Nov. 6, 2023

The N-functionalized indole is a privileged structural framework in wide range of bioactive molecules. nucleophilic addition between indoles with vinylene carbonate proceeded smoothly the presence K2CO3 as catalyst to produce novel indolyl-containing skeletons and 4-indolyl-1,3-dioxolanones satisfactory excellent yields (up >97% yield). Various synthetically useful functional groups, such halogen atoms, cyano, nitro, methoxycarbonyl remained intact during regioselective N-H reactions. developed catalytic system also could accommodate 2-naphthalenol achieve target O-H additive product good yield.

Language: Английский

---

Rh(III)‐Catalyzed C−H Annulation of 3‐Aryl‐2H‐benzo[e][1,2,4]thiadiazine‐1,1‐dioxides with Vinylene Carbonates

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 27(4)

Published: Nov. 22, 2023

Abstract A novel method has been developed for the synthesis of fused dihydroisoquinoline frameworks through a Rh(III)‐catalyzed annulation 3‐aryl‐2 H ‐benzo[ e ][1,2,4]thiadiazine‐1,1‐dioxides with vinylene carbonates by C−H bond activation. This is first report on oxidative functionalization aryl‐2 ][1,2,4]thiadiazine‐1,1‐dioxide carbonate to afford angularly heterocycles in good yields high functional group tolerance. In this approach, acts as glycolaldehyde surrogate construct ring systems.

Language: Английский

---

Theoretical investigation of Cp*Rh(III)-catalyzed allylation and cyclization reactions of 1-arylindazolones with carbonates

Chemical Physics Letters, Journal Year: 2024, Volume and Issue: 848, P. 141395 - 141395

Published: June 4, 2024

Language: Английский

---