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

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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

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Vinylene Carbonate as Synthon in Transition Metal‐Catalyzed C−H Bond Activation/Annulation Reactions

Advanced Synthesis & Catalysis, Journal Year: 2023, Volume and Issue: 365(20), P. 3400 - 3412

Published: Sept. 6, 2023

Abstract Recently, vinylene carbonate has been developed as a powerful synthon in transition metal‐catalyzed C−H bond activation/cyclization reactions. This review introduces recent progress the use of reactant, by analyzing and comparing reaction models involving surrogate ethynol, acetylene, acetylation reagents or other reactants, while addressing related mechanisms synthetic applications.

Language: Английский

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Divergent [5 + 1] Annulation of o-Aminobenzamides with Vinylene Carbonate as a Multifunctional Reagent

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

Published: April 3, 2025

A divergent [5 + 1] cyclization reaction of o-aminobenzamides with vinylene carbonate has been developed, rapidly generating three types cyclic molecules including quinazolinones, 2-methylquinazolinones, and 2,3-dihydroquinazolinones high chemoselectivity. In this discovery, blooms as a multifunctional reagent to participate in cyclization. The potential new finding is further emphasized by assembling the benzothiazole heteroarene via [4 version tolerating bioactive units well.

Language: Английский

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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

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Assembly of the Hydroxycinnoline Core via Hydrazide-Assisted Rh(III)-Catalyzed C–H Functionalization and Annulation

Synthesis, Journal Year: 2022, Volume and Issue: 54(20), P. 4461 - 4471

Published: March 30, 2022

Abstract The structural modification of phthalazinones and indazolones has emerged as a pivotal topic in catalytic C–H functionalization events. Herein we report the hydrazide-assisted rhodium(III)-catalyzed cross-coupling reactions N-arylphthalazinones N-arylindazolones with vinylene carbonate. This method provides direct access to tetracyclic hydroxycinnolines. Complete site-selectivity functional group compatibility were observed.

Language: Английский

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Synthesis of Succinimide-Linked Indazol-3-ols Derived from Maleimides under Rh(III) Catalysis

ACS Omega, Journal Year: 2022, Volume and Issue: 7(17), P. 14712 - 14722

Published: April 21, 2022

The structural modification of N-aryl indazolols as tautomers indazolones has been established a hot topic in pharmaceutics and medicinal chemistry. We herein disclose the rhodium(III)-catalyzed 1,4-addition reaction maleimides with indazol-3-ols, which provides succinimide-bearing indazol-3-ol scaffolds complete regioselectivity good functional group tolerance. Notably, versatility this protocol is demonstrated by use drug-molecule-linked fluorescence-probe-linked maleimides.

Language: Английский

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Rhodium‐Catalyzed C−H Activation/Annulation of N‐Aryl‐pyrazolidinones with Vinylene Carbonate

European Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 2022(19)

Published: April 21, 2022

Abstract A rhodium‐catalyzed C−H activation/annulation of N ‐aryl‐pyrazolidinones with vinylene carbonate was developed. The utilization as the acetylene surrogate furnished successful construction non‐substituted 5,6‐pyrazolo[1,2‐ a ]cinnoline derivatives, which are difficult to synthesize through other procedures. In this work, series variously substituted pyrazolo[1,2‐ ]cinnolines were obtained in yields up 98 % broad substrate scope and excellent selectivity. Moreover, external oxidants not required protocol H 2 O CO clean by‐products.

Language: Английский

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Rh(III)- or Ru(II)-Catalyzed C–H Annulation with Vinylene Carbonate and an Unexpected Aerobic Oxidation/Deprotection Cascade to Yield Cinnolin-4(1H)-ones

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

Published: Sept. 19, 2024

Transition metal-catalyzed C-H annulation reactions have been extensively utilized for the synthesis of cinnolines, especially N-protected ones; however, none them can yield cinnolin-4(1

Language: Английский

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Nitrogen-bridgehead compounds: overview, synthesis, and outlook on applications

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

Published: Dec. 3, 2024

Nitrogen bridgehead (NBH) is present in many natural products, but studies of synthetic analogues remain unexplored. This review gives an overview NBH for potential applications.

Language: Английский

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