Inherent directing group-enabled Co(iii)-catalyzed C–H allylation/vinylation of isoquinolones

Chemical Communications, Год журнала: 2024, Номер 60(43), С. 5626 - 5629

Опубликована: Янв. 1, 2024

Isoquinolones undergo efficient Co( iii )-catalyzed C8-allylation and vinylation, utilizing the oxo group of isoquinolones as an inherent directing group. The resulting allylated vinylated are further transformed into important building blocks.

Язык: Английский

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Reverse Regioselective Cp*Co(III)-Catalyzed [4 + 2] C–H Annulation of N-Chloroamides with Vinylsilanes: Synthesis of 4-Silylated Isoquinolones and Their Synthetic Utilities

Organic Letters, Год журнала: 2023, Номер 25(43), С. 7878 - 7883

Опубликована: Окт. 23, 2023

We have developed a Cp*Co(III)-catalyzed reverse regioselective [4 + 2] annulation of N-chlorobenzamides/acrylamides with vinylsilanes for the synthesis 4-silylated isoquinolones. The reaction was performed at ambient temperature under redox-neutral conditions. utilized N-Cl bond as an internal oxidant, furnished required products excellent regioselectivities, and demonstrated high functional group tolerance. synthetic utility isoquinolones has been preparation 4-heteroarylated 4-alkylated via metal-free C-C couplings. Additionally, 3,4-dihydroisoquinolones were synthesized protodesilylation isoquinolones, thus making vinylsilane ethylene surrogate.

Язык: Английский

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Recent developments for the synthesis of the dihydroisoquinolin-1(2H)-ones via cyclization of N-allylbenzamides

Tetrahedron, Год журнала: 2025, Номер unknown, С. 134497 - 134497

Опубликована: Янв. 1, 2025

Язык: Английский

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Progress on Cobalt-Catalyzed C(sp²)—H Activation for the Construction of Nitrogen-Containing Benzo Heterocycles

Chinese Journal of Organic Chemistry, Год журнала: 2025, Номер 45(2), С. 655 - 655

Опубликована: Янв. 1, 2025

Язык: Английский

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Green Synthesis of 3,4‐Unsubstituted Isoquinolones through Rhodium(III)‐Catalyzed C−H Activation and Annulation in Ethanol

European Journal of Organic Chemistry, Год журнала: 2023, Номер 26(44)

Опубликована: Сен. 27, 2023

Abstract A mild and convenient synthesis of 3,4‐unsubstituted isoquinolones has been achieved from N ‐methoxybenzamides vinylene carbonate as an acetylene surrogate with a versatile rhodium(III) catalyst. The reaction proceeded at room temperature in biomass derived ethanol solvent. This protocol avoids the use stoichiometric external oxidant, served internal oxidant. C−H/N−H activation annulation manifold broad substrate scope excellent levels regioselectivities. preliminary mechanistic studies suggest facile reversible chelation‐assisted C−H rhodation. Diversification provide access to 4‐substituted isoquinolines, which are complementary previously reported protocols.

Язык: Английский

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Harnessing Vinyl Acetate as an Acetylene Equivalent in Redox-Neutral Cp*Co(III)-Catalyzed C–H Activation/Annulation for the Synthesis of Isoquinolones and Pyridones

ACS Omega, Год журнала: 2023, Номер 8(28), С. 25262 - 25271

Опубликована: Июль 5, 2023

We have developed Cp*Co(III)-catalyzed redox-neutral synthesis of 3,4-unsubstituted isoquinoline 1(2H)-ones at ambient temperature using N-chloroamides as a starting material. The reaction utilizes vinyl acetate an inexpensive and benign acetylene surrogate. N-Cl bond the N-chlorobenzamides plays role internal oxidant hence precludes need for external oxidant. works with wide range substrates having various functional groups substrate containing heterocyclic ring. Notably, is extended to N-chloroacrylamides in which vinylic C-H activation occurs furnish 2-pyridone derivatives. Preliminary mechanistic studies were also conducted shed light on mechanism this reaction.

Язык: Английский

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Recent Advances in the 3 d‐Transition‐Metal‐Catalyzed Synthesis of Isoquinolines and its Derivatives

Advanced Synthesis & Catalysis, Год журнала: 2023, Номер 365(24), С. 4458 - 4494

Опубликована: Ноя. 24, 2023

Abstract The preservation of scarce rare earth metals, such as palladium, rhodium, iridium, and others, poses a significant challenge for humanity due to their limited availability. These metals might be replaced by earth‐abundant 3d‐transition cobalt, manganese, iron, nickel, copper, etc . Isoquinolines have acquired an important position in synthetic organic chemistry well medicinal chemistry. They manifest diverse range natural molecules, serving pivotal synthons the synthesis numerous bioactive compounds with notable significance. Numerous reports on isoquinoline derivatives via transition metal catalysis been published worldwide. In this review, we summarize recent approaches synthesizing various using 3d‐transition‐metal catalysts since 2020. review has divided into different 3d‐transition‐metal‐based catalysis. We expect that will bring better overview present status progress made isoquinolines persuade more advancements research area near future.

Язык: Английский

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

RSC Advances, Год журнала: 2024, Номер 14(7), С. 4804 - 4809

Опубликована: Янв. 1, 2024

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

Язык: Английский

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Co(III)-Catalyzed C6-Selective C–H Activation/Pyridine Migration of 2-Pyridones with Propiolates

Organic Letters, Год журнала: 2023, Номер unknown

Опубликована: Дек. 21, 2023

A versatile Co(III)-catalyzed C6-selective C–H activation/pyridine migration of 2-pyridones with available propiolates as coupling partners was demonstrated. This method features high atom economy, excellent regioselectivity, and good functional group tolerance by employing an inexpensive Co(III) catalyst under mild reaction conditions. Moreover, gram-scale synthesis late-stage modifications pharmaceuticals were performed to prove the effectiveness these synthetic approaches.

Язык: Английский

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Vinyl Esters and Vinyl Sulfonates as Green Alternatives to Vinyl Bromide for the Synthesis of Monosubstituted Alkenes via Transition-Metal-Catalyzed Reactions

Chemistry, Год журнала: 2023, Номер 5(4), С. 2288 - 2321

Опубликована: Окт. 20, 2023

This review summarizes the applications of vinyl sulfonate and acetate as green alternatives for bromide in cross-coupling reactions. In first part, preparation sulfonates their reactions are briefly discussed. Then, a brief reactions, including cyclization Fujiware–Moritani reaction, transvinylation described.

Язык: Английский

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