Synthesis of Sulfilimines via Multicomponent Reaction of Arynes, Sulfamides, and Thiosulfonates

Organic Letters, Journal Year: 2023, Volume and Issue: 25(33), P. 6133 - 6138

Published: Aug. 14, 2023

In this work, a facile and efficient method for the synthesis of sulfilimines through multicomponent reaction arynes, sulfamides, thiosulfonates was developed. A variety structurally diverse substrates functional groups were very compatible in reaction, giving corresponding good to high yields. This protocol could be conducted on gram scale, product easily converted sulfide sulfoximine. Mechanism studies revealed that sulfenamide generated situ is key intermediate reaction.

Language: Английский

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Synthesis of Trisubstituted Oxazoles via Aryne Induced [2,3] Sigmatropic Rearrangement–Annulation Cascade

Organic Letters, Journal Year: 2022, Volume and Issue: 24(23), P. 4145 - 4150

Published: June 6, 2022

A transition-metal-free, [2,3] sigmatropic rearrangement-annulation cascade of 2-substituted thio/amino acetonitriles with arynes allowing the synthesis 2,4,5-trisubstituted oxazoles under mild conditions has been demonstrated. The key sulfur/nitrogen ylides were generated by initial S/N arylation followed proton transfer, which was selective rearrangement involving -CN moiety and a subsequent annulation to afford desired products in reasonable yields.

Language: Английский

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Divergent Construction of α,α-Difunctionalized Ketones via [1,2]-Sigmatropic Rearrangement/Alkylation-Hydroxylation/Dialkylation of I^(III)/S^(VI) Ylides

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

Published: April 1, 2025

The rare [1,2]-sigmatropic rearrangement of sulfoxonium-iodonium hybrid ylides is described, which enables the efficient sulfoxidation/sulfonylation-alkylation I(III)/S(VI) with 1,3-dicarbonyls. By slight modification reaction conditions, controllable alkylation-hydroxylation and dialkylation were achieved. This strategy affords a diverse array α,α-difunctionalized ketones in moderate to good yields, demonstrating broad substrate scope. These findings provide an important advancement sulfoxonium highlight divergent reactivity ylides.

Language: Английский

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Recent Advances in Construction of C(sp2)–O Bonds via Aryne Participated Multicomponent Coupling Reactions

Synthesis, Journal Year: 2022, Volume and Issue: 54(22), P. 5064 - 5076

Published: Jan. 24, 2022

Abstract Aryne chemistry is a powerful synthetic technique that forms new bonds to aromatic rings. The recent resurgence of aryne-based multicomponent coupling strategies has led an influx methodologies for the mild synthesis arene derivatives. In particular, these innovative discoveries broaden and streamline approaches toward phenol ether motifs, which are prevalent structural component across broad range related research fields. Herein, this review aims provide comprehensive overview progress in construction C(sp2)–O via aryne-induced reactions. Special attention been paid reaction design mechanistic pathways. 1 Introduction 2 Insertion-Based MCRs 3 Nucleophilic-Addition-Based 4 Cycloaddition-Based 5 Summary

Language: Английский

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Access to diverse organosulfur compounds via arynes: a comprehensive review on Kobayashi's aryne precursor

Organic & Biomolecular Chemistry, Journal Year: 2021, Volume and Issue: 19(39), P. 8466 - 8481

Published: Jan. 1, 2021

Arynes are highly reactive transient intermediates having enormous applications in organic synthesis. In the last three decades aryne chemistry has shown incredible developments carbon-carbon and carbon-heteroatom bond formation reactions. After discovery of Kobayashi's protocol for generation a mild way, this field witnessed rapid growth synthetic chemistry. One aspect development involves C-S under conditions which tremendous scope synthesis various important organosulfur building blocks.

Language: Английский

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Construction of 6H-benzo[c]thiochromenes via a tandem reaction of arynes with thionoesters

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(24), P. 6979 - 6984

Published: Jan. 1, 2021

A mild and transition-metal free method has been proposed for the synthesis of 6 H -benzo[ c ]thiochromenes via tandem reactions arynes with thionoesters.

Language: Английский

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Reactivity of Vinyl Epoxides/Oxetanes/Cyclopropanes toward Arynes: Access to Functionalized Phenanthrenes

ACS Omega, Journal Year: 2021, Volume and Issue: 6(51), P. 35852 - 35865

Published: Dec. 15, 2021

The reactivity of vinyl epoxides/oxetanes/cyclopropanes toward arynes has been demonstrated under mild conditions to give the corresponding phenanthrenes in moderate good yields. This transition-metal-free cascade process involves a series Diels-Alder reaction, ring-opening aromatization, and ene reaction. Various functionalized could be synthesized utilizing versatile hydroxy group. Interestingly, epoxides/oxiranes experience preferentially reaction over nucleophilic attack epoxides/oxiranes.

Language: Английский

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Synthesis of C2‐Functionalized Pyrimidine Derivatives by Using Arynes and Dithiopyrimidines

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(29)

Published: July 14, 2023

Abstract C2‐functionalized pyrimidine derivative is a family of important nitrogen heterocyclic compounds due to their unique structure and multiple reaction sites. In this work, novel method for the synthesis derivatives through phenylalkynes disulfides under ambient conditions proposed. The can be triggered by adding catalytic amounts cesium fluoride, which characterized free‐catalyst special activator. Importantly, has good compatibility with substrates substituted electron‐donating electron‐withdrawing groups at C4. Density functional theory (DFT) calculations also indicates that production more favourable.

Language: Английский

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Synthesis of Tritylones via Cascade Reaction of Arynes with 5-Ethoxyoxazoles

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(11), P. 7219 - 7228

Published: May 17, 2022

A cascade reaction involving arynes and 5-ethoxyoxazoles has been developed toward the synthesis of 9-alkyl/aryl tritylones. 5-Ethoxyoxazoles undergo a [4 + 2] cycloaddition with followed by retro-[4 cycloaddition, second intermolecular reaction, hydrolytic ring cleavage to generate substituted tritylones in good yields. The conversion tritylone products series spirocyclic anthrone derivatives demonstrated. is expeditious, exhibits wide scope, employs readily available starting materials.

Language: Английский

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Synthesis of P‐Arylphosphinecarboxamide Derivatives by Addition of N‐Arylphosphinecarboxamides with Aryne Precursors

Asian Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 11(8)

Published: May 12, 2022

Abstract A reliable method for preparing P (III)‐arylphosphinecarboxamide derivatives from N ‐arylphosphinecarboxamides and aryne precursors has been developed. This reaction was carried out without transition‐metal catalysts, a series of unsymmetrically structured phosphinecarboxamide were obtained under mild conditions. In addition, the is air atomosphere, corresponding P(III)‐aryl compounds are also stable in air.

Language: Английский

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