Applications of sulfonyl hydrazides in radical cyclization of alkenes

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(29), P. 5906 - 5918

Published: Jan. 1, 2023

We highlighted the applications of sulfonyl hydrazides in radical cyclization alkenes, which generally has two conversion modes, including radicals and sulfoxide radicals, with an emphasis on their reaction mechanisms.

Language: Английский

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Catalyst-free electrochemical trifluoromethylation of coumarins using CF₃SO₂NHNHBoc as the CF₃ source

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(9), P. 1883 - 1887

Published: Jan. 1, 2023

An efficient electrochemical trifluoromethylation of coumarins using CF 3 SO 2 NHNHBoc as the source trifluoromethyl group was developed.

Language: Английский

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Regulation of Photogenerated Redox Species through High Crystallinity Carbon Nitride for Improved C−S Coupling Reactions

ChemSusChem, Journal Year: 2024, Volume and Issue: 17(10)

Published: Jan. 20, 2024

Abstract A novel and efficient approach for the synthesis of α, β‐unsaturated sulfones through heterogeneous photocatalyzed C−S coupling reactions have been developed. The use molten‐salt method derived carbon nitride (MCN), a transition metal‐free polymeric photocatalyst, combined with enhanced crystallinity potassium iodide as an additive, effectively modulates photogenerated reactive redox species, markedly increasing overall reaction selectivity. This achieves shortest time (2 h) high yield (up to 95 %) among reported catalytic bond formation reactions, matching efficiency homogeneous photocatalysts. Furthermore, application challenging alkyne substrates has demonstrated, underscoring potential broad range applications in pharmaceutical research synthetic chemistry.

Language: Английский

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Zinc Promoted Cross‐Electrophile Sulfonylation to Access Alkyl–Alkyl Sulfones

Advanced Science, Journal Year: 2024, Volume and Issue: 11(32)

Published: July 4, 2024

Abstract The transition metal‐catalyzed multi‐component cross‐electrophile sulfonylation, which incorporates SO 2 as a linker within organic frameworks, has proven to be powerful, efficient, and cost‐effective means of synthesizing challenging alkyl–alkyl sulfones. Transition metal catalysts play crucial role in this method by transferring electrons from reductants electrophilic organohalides, thereby causing undesirable side reactions such homocoupling, protodehalogenation, β ‐hydride elimination, etc. It is worth noting that tertiary alkyl halides have rarely been demonstrated compatible with current methods owing various undesired reactions. In work, zinc‐promoted sulfonylation developed through radical‐polar crossover pathway. This approach enables the synthesis sulfones, including 1°‐1°, 2°‐1°, 3°‐1°, 2°‐2°, 3°‐2° types, inexpensive readily available halides. Various functional groups are well tolerated resulting yields up 93%. Additionally, protocol successfully applied intramolecular homo‐sulfonylation insights gained work shall useful for further development access

Language: Английский

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Visible-Light-Induced Cascade Cyclization of 1-(2-(Arylethynyl)benzoyl)indoles into Sulfonated Benazepino[1,2-a]indolones

Organic Letters, Journal Year: 2024, Volume and Issue: 26(50), P. 10982 - 10987

Published: Dec. 10, 2024

1-(2-(Arylethynyl)benzoyl)indoles were developed as an innovative scaffold for radical cascade cyclization under visible-light and mild conditions, enabling efficient synthesis of sulfonated benazepino[1,2-

Language: Английский

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Progress in S–X Bond Formation by Halogen-Mediated Electrochemical Reactions

Synthesis, Journal Year: 2023, Volume and Issue: 55(18), P. 2799 - 2816

Published: May 19, 2023

Abstract Sulfur-containing compounds are very common and important heteroatom skeletons widely found in natural products, pharmaceuticals bioactive compounds. Moreover, the development of synthetic routes to organosulfur has attracted considerable attention due their wide range applications organic chemistry, pharmaceutical industry materials science. As one most powerful, green eco-friendly research areas, electrosynthesis, contrast conventional synthesis, can avoid use harmful stoichiometric external oxidants or reductants. Importantly, halide salts used as supporting electrolytes redox catalysts indirect electrosynthesis limitations imposed by high overpotentials direct electrosynthesis. In recent years, significant progress been made on halogen-mediated this review, scope, mechanisms electrochemical transformations sulfur-containing presented discussed. 1 Introduction 2 S–C Bond Formation 2.1 Organic Thiocyanates 2.2 Sulfonyl Compounds 2.3 Other Sulfides 3 S–X (X = N, O, S, P) Bonds 4 Conclusion Outlook

Language: Английский

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An Efficient Electrochemical Synthesis of Selenocarbamates from Isocyanates and Diselenides

ChemistrySelect, Journal Year: 2024, Volume and Issue: 9(32)

Published: Aug. 22, 2024

Abstract A facile electrochemical synthesis of selenocarbamates from multicomponent reactions isocyanides, diselenides, and water is developed here. This strategy provides a mild, direct, complementary approach for synthesizing in moderate to excellent yields with good substrate tolerance. The simple undivided cell setting carbon/Pt electrodes proceeded smoothly. radical pathway was proposed by preliminary mechanistic research.

Language: Английский

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Cyclic sulfones from double conjugate addition of Rongalite

Synthetic Communications, Journal Year: 2023, Volume and Issue: 53(16), P. 1351 - 1359

Published: June 9, 2023

AbstractCyclic sulfones are obtained in up to 92% yield by double conjugate addition of Rongalite (sodium hydroxymethyl sulfinate) dienones. The major product each case is the kinetic trans-isomer 3,5-disubstituted ketosulfone. Eleven examples, including aryl and alkyl substituted substrates, reported. advantages method its experimental simplicity, tolerance for both protic oxidation-sensitive functional groups, sterically challenging substrates. work also significantly expands scope as a nucleophile.Keywords: Conjugate additiondienonesRongalitesulfones AcknowledgmentsS. Finn R. Murtada (Montclair State) acknowledged mass spectra Dr N. Dayal Prof. H. Sintim (Purdue University).Additional informationFundingWe thank Montclair State University startup funds, NSF an MRI grant (# 2116596, PI Dr. J. Gao, University), ACS Petroleum Research Fund additional financial support (Grant #65204-UR1).

Language: Английский

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Synthesis of N-Acyl-N’-Sulfonyl Hydrazides from Sulfonyl Hydrazides and Activated Amides

Synthesis, Journal Year: 2024, Volume and Issue: 56(22), P. 3468 - 3474

Published: July 16, 2024

Abstract A methodology was developed for synthesizing N-acyl-N'-sulfonyl hydrazides through acyl substitution reactions between activated amides and arylsulfonyl hydrazides. Optimization of the reaction conditions revealed that using Cs₂CO₃ as a base 1,4-dioxane solvent at 25 °C 12 hours produced highest yields. Among various tested, N-benzoylsuccinimide found to be most reactive, with reduced reactivity observed N-mesityl-, N-tosyl-, N-Boc-substituted tertiary benzoyl amides. Cross-reactions diverse range N-benzoylsuccinimides successfully corresponding N-acyl-N′-sulfonyl yields ranging from 63% 94%.

Language: Английский

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Electrochemical sulfonylation/Truce–Smiles rearrangement of N-allylbenzamides: toward sulfone-containing β-arylethylamines and Saclofen analogues

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(40), P. 8102 - 8108

Published: Jan. 1, 2024

A practical electrochemical sulfonylation-triggered Truce–Smiles rearrangement of N -allylbenzamides yielded sulfone- and sulfonic acid-containing β-arylethylamines under mild oxidant-free reaction conditions.

Language: Английский

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