Base-Promoted Regioselective Annulation of Pyridinium Ylides and Bromoalkynes for the Chemodivergent Synthesis of Indolizines

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

Published: Feb. 5, 2025

A base-promoted regioselective formal [3 + 2] annulation of pyridinium ylides with bromoalkynes is reported, producing a series substituent-diverse indolizines in generally good yields. mild K2CO3-promoted three-component cyclization and at 2:1 molar ratio delivered C2-acylmethylated indolizines, whereas C2-brominated were generated starting from bearing strong electron-withdrawing groups the unit by using 2,2,6,6-tetramethyl-1-piperidinyloxy as dehydrogenating reagent. The current synthetic methodology offers controllable modular approach to access different substitution patterns, featuring wide substrate scope, functional group compatibility, complete regioselectivity without demand any transition-metal catalysts.

Language: Английский

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Catalytic C H activation-initiated transdiannulation: An oxygen transfer route to ring-fluorinated tricyclic γ-lactones

Chinese Chemical Letters, Journal Year: 2024, Volume and Issue: 35(9), P. 109494 - 109494

Published: Jan. 6, 2024

Language: Английский

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Nickel-catalysed chelation-assisted reductive defluorinative sulfenylation of trifluoropropionic acid derivatives

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(17), P. 2405 - 2408

Published: Jan. 1, 2024

Nickel-catalysed chelation-assisted reductive cross-coupling of trifluoropropanamides/esters with disulfides to afford thioacrylamides/esters high E selectivity, involving triple C–F bond cleavage.

Language: Английский

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Experimental and computational journey on transition-metal-catalyzed C H functionalization with fluorinated π-systems

Coordination Chemistry Reviews, Journal Year: 2024, Volume and Issue: 522, P. 216244 - 216244

Published: Sept. 24, 2024

Language: Английский

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Enantioselective synthesis of saddle-shaped eight-membered lactones with inherent chirality via organocatalytic high-order annulation

Nature Communications, Journal Year: 2024, Volume and Issue: 15(1)

Published: Oct. 1, 2024

Language: Английский

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Cu(II)-Catalyzed Annulative Sulfonylimination of α-Carbonyl-γ-alkynyl Sulfoxonium Ylides through Sulfoxonium Ylide Elimination for Access to (Z)-1H-Isochromenes

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(4), P. 1663 - 1670

Published: Jan. 21, 2025

1H-Isochromene scaffolds are ubiquitous in natural products and significant bioactive molecules. Although several methods for these molecular syntheses have been developed, reports on the efficient construction of iminated isochromenes still rather limited. Herein, we report a new Cu(II)-catalyzed annulation sulfonylimination cascade α-carbonyl-γ-alkynyl sulfoxonium ylides with sulfamides, enabling direct C-C σ-bond elimination to furnish (Z)-1H-isochromenes 51-97% yields. During reaction process, ylide unit as traceless eliminative group is key successful sulfonylimination, which enables N-H insertion subsequent acetic acid-mediated elimination.

Language: Английский

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Catalytic Schmittel-Type [2+2] Cycloaddition of γ-Alkynyl Diazoacetates with Terminal Alkynes for Accessing Cyclobuta[a]indenes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: March 17, 2025

Instead of the conventional [4+2] cycloaddition, a regioselective Schmittel-type [2+2] cycloaddition yne–allene esters, generated in situ from copper-catalyzed dediazotized coupling γ-alkynyl diazoacetates with terminal alkynes, is reported, enabling bicyclization process to produce diverse array C1-arylated cyclobuta[a]indenes moderate good yields. The protocol features wide functional group compatibility, mild reaction conditions, and experimental simplicity, holding significant potential for building new tricyclic cyclobutenes.

Language: Английский

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Allylic Acetal as 3C Synthon in Rh(III)-Catalyzed Divergent C–H Activation/[4 + 3] Annulation: Easy Access to Benzodiazepines

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 2, 2025

A concise synthesis of benzodiazepines via Rh(III) catalyzed C-H activation/ [4 + 3] annulation easily available 1-arylpyrazolidinones with allylic acetal has been developed. The was employed as a novel 3C synthon in this transformation. Benzodiazepines were built under mild reaction conditions high efficiency and chemoselectivity. atom-economy accessible substrates reveal potential application.

Language: Английский

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Synthesis of gem-difluorinated pentacyclic indenopyrazolopyrazolones via Rh(iii)-catalyzed cascade C–H functionalization/[3 + 2] dipolar cycloaddition

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(9), P. 2512 - 2517

Published: Jan. 1, 2024

A Rh( iii )-catalysed cascade C–H functionalization/[3 + 2] dipolar cycloaddition was realized to deliver gem -difluorinated pentacyclic indenopyrazolopyrazolones with four continuous chiral carbon centres in a one-pot fashion.

Language: Английский

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PhI(OAc)₂-mediated aminoacyloxylation of β,γ-unsaturated hydrazones using Togni reagent II as an acyloxyl precursor

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(33), P. 6757 - 6761

Published: Jan. 1, 2023

A metal-free protocol for the direct construction of C(sp2)-N and C-O bonds via a PhI(OAc)2-mediated dehydrogenative aminoacyloxylation β,γ-unsaturated hydrazones with Togni reagent II is reported. Initiated by carboxyl-containing species generated in situ from II, this method offers new solution regioselective functionalization at remote site on hydrazones, thus providing straightforward synthesis acyloxyl-substituted pyridazines. This reaction features broad substrate scope mild conditions.

Language: Английский

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