Recent advances in visible light-mediated chemical transformations of enaminones

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(2), P. 108977 - 108977

Published: Aug. 26, 2023

Language: Английский

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Carbon-carbon triple bond cleavage and reconstitution to achieve aryl amidation using nitrous acid esters

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Jan. 24, 2025

C–C bond cleavage and recombination provide an efficient strategy for the modification reconstruction of molecule structures. Herein, we present a method achieving amidation aryl C(sp2)–H through triple with involvement nitrous acid esters. This marks instance precise controlled stepwise bond, offering fresh perspective such bonds. Nitrous ester serves as both radical source hydrogen atom transfer (HAT) reagent to functionalize utilize two carbon atoms bond. The alkoxy captures from or N-hydroxyl induce 1,3-oxygen migration, which is crucial subsequent molecular authors report achieve bonds by participation

Language: Английский

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Synthesis of Tetrahydro-indolones through Rh(III)-Catalyzed [3 + 2] Annulation of Enaminones with Iodonium Ylides

Organic Letters, Journal Year: 2023, Volume and Issue: 25(40), P. 7298 - 7303

Published: Oct. 3, 2023

An unprecedented protocol for a Rh(III)-catalyzed [3 + 2] annulation from simple and readily available enaminones iodonium ylides has been developed. The novel strategy allows access to new class of structurally diverse tetrahydro-indolones with high efficiency broad substrate scope. In addition, this transformation represents the first example selective alkenyl C–H bond functionalization enaminones. Finally, potential applications are demonstrated through gram-scale reaction late-stage modification.

Language: Английский

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Rh(III)-Catalyzed [3 + 2] Annulation/Pinacol Rearrangement Reaction of Enaminones with Iodonium Ylides: Direct Synthesis of 2-Spirocyclo-pyrrol-3-ones

Organic Letters, Journal Year: 2023, Volume and Issue: 25(39), P. 7214 - 7219

Published: Sept. 26, 2023

A novel Rh(III)-catalyzed cascade alkenyl C-H activation/[3 + 2] annulation/pinacol rearrangement reaction of enaminones with iodonium ylides has been developed. This methodology provides a new and straightforward synthetic strategy to afford highly functionalized 2-spirocyclo-pyrrol-3-ones in satisfactory yield from readily available starting materials under mild conditions. Moreover, gram-scale reactions further derivatization experiments are implemented demonstrate the potential utility this developed approach.

Language: Английский

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Recent advances in transition metal-catalyzed transformations in N,N-disubstituted enaminones

Tetrahedron Letters, Journal Year: 2023, Volume and Issue: 130, P. 154766 - 154766

Published: Sept. 26, 2023

Language: Английский

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Transition metal-free tunable synthesis of 3-(trifluoromethylthio) and 3-trifluoromethylsulfinyl chromones via domino C-H functionalization and chromone annulation of enaminones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(11), P. 109683 - 109683

Published: March 2, 2024

Language: Английский

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Iodine-Promoted Thioylation and Dicarbonylation of Enaminone α-C Sites: Synthesis of Fully Substituted Thiazoles via C═C Bond Cleavage

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(4), P. 2505 - 2515

Published: Feb. 5, 2024

A novel iodine-promoted difunctionalization of α-C sites in enaminones was demonstrated as a means synthesizing variety fully substituted thiazoles by constructing C–C(CO), C–S, and C–N bonds. This transformation allows the realization unusual aryl C2 synthons simultaneously thioylation dicarbonylation sites. preliminary mechanistic study performed indicated that cleavage C═C bonds involves bicyclization/ring-opening oxidative coupling sequence.

Language: Английский

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Silver‐catalyzed Cascade Bis‐heteroannulation Reaction of Enynones and o‐Hydroxyphenyl Enaminones: Access to Highly Functionalized 3‐Furylmethyl Chromones

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(10), P. 2363 - 2369

Published: March 16, 2024

Abstract A synthetic protocol was developed to synthesize highly functionalized 3‐furylmethyl chromones from enynones and o ‐hydroxyphenyl enaminones via silver‐catalyzed cascade bis‐heteroannulation reaction. This strategy features broad substrate scope good functional group tolerance. Furthermore, the chromone skeleton shows potential application value through further gram‐scale synthesis derivatization.

Language: Английский

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Unprecedented chemoselective Ru(iii)-catalyzed [3 + 2] annulation of enaminones with iodonium ylides for the synthesis of functionalized 3a,7a-dihydroxy hexahydro-4H-indol-4-ones

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(22), P. 5660 - 5666

Published: Jan. 1, 2023

Highly functionalized 3a,7a-dihydroxy hexahydro-4 H -indol-4-ones were efficiently synthesized via a Ru( iii )-catalyzed alkenyl C(sp 2 )–H bond functionalization/[3 + 2] annulation reaction between readily available enaminones and iodonium ylides.

Language: Английский

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Annulative Nonaromatic Newman–Kwart-Type Rearrangement for the Synthesis of Sulfur Heteroaryls

Organic Letters, Journal Year: 2023, Volume and Issue: 26(1), P. 46 - 50

Published: Dec. 27, 2023

By employing enaminones and thiuram disulfides as starting materials, the frontiers of Newman–Kwart rearrangement have been expanded to alkenyl system for first time. In addition, instead leading formation simple carbamothioates, has led unprecedented construction S-heteroaryls. Depending on differences in enaminone structure, efficient synthesis functionalized isothiazoles thiophenes achieved.

Language: Английский

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