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

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(43), P. 5626 - 5629

Published: Jan. 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.

Language: Английский

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Ru(II)‐Catalyzed Selective C—H Alkynylation of Isoquinolones, Quinazolones and Phthalazinones with Bromoalkynes

Chinese Journal of Chemistry, Journal Year: 2024, Volume and Issue: 42(15), P. 1686 - 1690

Published: March 15, 2024

Comprehensive Summary A new, selective Ru(II)‐catalyzed alkynylation reaction of isoquinolones, quinazolones and phthalazinones with readily available bromoalkynes has been developed. This enables the construction a new C(sp 2 )‐C(sp) bond through C—H activation C—Br functionalization, offers an effective route to synthesizing highly valuable alkynylated isoquinolone, quinazolone phthalazinone derivatives wide substrate scope high selectivity.

Language: Английский

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Co(III)-Catalyzed Regioselective Functionalization of Isoquinolones with Naphthoquinones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(23), P. 5027 - 5031

Published: June 3, 2024

A strategy for Co(III)-catalyzed C(sp

Language: Английский

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Rh(III)-Catalyzed Regioselective C(sp2)-H alkenylation of isoquin-olones with methoxyallene: A Facile Access to aldehyde bearing iso-quinolones

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(32), P. 6612 - 6616

Published: Jan. 1, 2024

A simple and rapid access to isoquinolone aldehyde scaffolds has been established by a rhodium-catalyzed reaction between methoxyallene that forges alkenylation in an explicit regioselective manner. Herein, serving as acrolein equivalent results execution of this unique functionalization. Furthermore, the compatibility with complex molecules underscores significance developed protocol. The mechanistic proposal for transformation was consistent kinetic studies several control reactions.

Language: Английский

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Rh(III)-Catalyzed Regioselective C8-alkenylation of isoquinolones with methoxyallene: A Facile Access to aldehyde bearing isoquin-olones

Published: Feb. 21, 2024

A simple and facile access to isoquinolone aldehyde scaffolds has been achieved through a rhodium-catalyzed reaction between methoxyallene. Herein, methoxyallene serves as an acrolein equivalent, resulting in this unique functionalization. Furthermore, the compatibility with natural complex drug molecules underscores sig-nificance of developed protocol. Based on kinetic studies several control reactions, plausible mecha-nism also proposed for regioselective transformation.

Language: Английский

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Ru(II)-Catalyzed C7 Trifluoromethylthiolation and Thioarylation of Indolines Using Bench-Stable Reagents

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(21), P. 15893 - 15900

Published: Oct. 16, 2024

A Ru(II)-catalyzed C(sp2)-H trifluoromethylthiolation and thioarylation of indolines using bench-stable reagents have been explored. Diversely substituted were functionalized at C7 position in good to excellent yields. Radical quenching, deuterium labeling, KIE, reaction order determination experiments performed support the proposed pathway. Gram-scale synthesis post-transformation synthesized products also carried out demonstrate applicability developed catalytic protocol.

Language: Английский

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Co(III) ‐Catalyzed Regioselective [4+2]‐Annulation of N‐Chlorobenzamide with Allenes and Vinyl Acetate

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 13(1)

Published: Nov. 28, 2023

Abstract A regioselective annulation protocol of N ‐chlorobenzamide with allenes and vinyl acetate is reported using a less expensive catalytic system, i. e . Co(III) catalysis Na 2 CO 3 as base. (CO) NH−Cl acts both, an internal oxidant directing group. Allenes are successfully annulated ‐chlorobenzamide, providing different exocyclic isoquinolone derivatives in good to moderate yield. Notably, acetylene surrogate undergoes the developed provide excellent Interestingly, situ deprotection acetyl group allowed quantitative synthesis hydroxyisoquinolone.

Language: Английский

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Ru(II)‐Catalyzed C8 Alkenylation of Isoquinolones with Allyl Alcohol

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

Published: Aug. 9, 2024

Abstract A simple Ru(II)‐catalyzed protocol for the alkenylation of isoquinolones with readily accessible allyl alcohols to generate aldehyde bearing has been developed. The use green solvent like dimethyl carbonate makes this method environment‐friendly. Experimental studies were carried out support proposed mechanism. reaction was scaled up showcase application current method.

Language: Английский

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Unveiling the role of aniline as a Brønsted base in Rh-catalyzed C−H alkylation: Computational insights into amino-assisted outer-sphere CMD

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 572, P. 114715 - 114715

Published: Nov. 28, 2024

Language: Английский

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Cobalt Catalysis: C7 Alkynylation of Indolines with a Bromoalkyne

Synthesis, Journal Year: 2023, Volume and Issue: 56(05), P. 751 - 757

Published: Nov. 28, 2023

Abstract A method for the cobalt-catalyzed C-7 alkynylation of indolines with (bromoethynyl)triisopropylsilane under mild conditions is described, leading to a diverse range alkynylated in good excellent yields. Kinetic isotope studies indicate that formation cobaltacycle might be turnover-limiting step. Additionally, gram-scale synthesis and oxidation an indoline indole have been carried out successfully

Language: Английский

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