Organoelectrocatalysis Enables Direct Cyclopropanation of Methylene Compounds

Journal of the American Chemical Society, Journal Year: 2022, Volume and Issue: 144(5), P. 2343 - 2350

Published: Feb. 1, 2022

Cyclopropane is a prevalent structural unit in natural products and bioactive compounds. While the transition metal-catalyzed alkene cyclopropanation of functionalized compounds such as α-diazocarbonyl derivatives has been well established provides straightforward access to cyclopropanes, directly from more stable simpler methylene remained an unsolved challenge despite highly desirable benefits minimal prefunctionalization increased operational safety. Herein we report electrocatalytic strategy for active compounds, employing organic catalyst. The method shows broad substrate scope excellent scalability, requires no metal catalyst or external chemical oxidant, convenient several types cyclopropane-fused heterocyclic carbocyclic Mechanistic investigations suggest that reactions proceed through radical-polar crossover process form two new carbon-carbon bonds nascent cyclopropane ring.

Language: Английский

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C(sp³)–H/C(sp³)–H Dehydrogenative Radical Coupling of Glycine Derivatives

Organic Letters, Journal Year: 2022, Volume and Issue: 24(41), P. 7577 - 7582

Published: Oct. 10, 2022

Here we report a general C(sp3)–H/C(sp3)–H dehydrogenative coupling strategy for the preparation of various natural or unnatural amino acids from readily available glycine derivatives and hydrocarbons through combination SET HAT process.

Language: Английский

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Electrochemical Annulation of Indole-Tethered Alkynes Enabling Synthesis of Exocyclic Alkenyl Tetrahydrocarbazoles

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(11), P. 6962 - 6972

Published: May 22, 2023

An electrochemical sulfonylation-triggered cyclization reaction of indole-tethered terminal alkynes with sulfinates as sulfonyl sources has been developed, which affords exocyclic alkenyl tetrahydrocarbazoles in good chemical yields. This features convenient operation and tolerates a wide scope substrates variety electronically sterically diverse substituents. Furthermore, high E-stereoselectivity is observed for this reaction, provides an efficient method the preparation functionalized tetrahydrocarbazole derivatives.

Language: Английский

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The synthesis of seven- and eight-membered rings by radical strategies

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(17), P. 4757 - 4781

Published: Jan. 1, 2022

Radical strategies for preparation of seven- or eight-membered rings.

Language: Английский

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Electrochemical oxidative synthesis of 1,3,4-thiadiazoles from isothiocyanates and hydrazones

Organic Chemistry Frontiers, Journal Year: 2021, Volume and Issue: 8(10), P. 2208 - 2214

Published: Jan. 1, 2021

A metal- and oxidant-free electrosynthesis of 2-amino-1,3,4-thiadiazoles through tandem addition/chemoselective C–S coupling.

Language: Английский

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Heterogeneous visible-light promoted dehydrogenative [4 + 2] annulation of benzothioamides and alkynes under aerobic conditions

Green Chemistry, Journal Year: 2023, Volume and Issue: 25(13), P. 5206 - 5212

Published: Jan. 1, 2023

We have developed a visible-light induced dehydrogenative [4 + 2] annulation of benzothioamides and alkynes under aerobic conditions to synthesize isothiochromenes.

Language: Английский

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Radical-polar Crossover Reaction of Glycine Derivatives

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(75), P. 10378 - 10381

Published: Jan. 1, 2024

Here we report a visible-light facilitated radical addition strategy for the preparation of various natural or unnatural α-amino acids from readily available glycine derivatives and alkenes. A key aspect in achieving this side carbon chain introduction reaction, while circumventing well-documented cyclization pathway, was employment radical-polar crossover under redox neutral conditions.

Language: Английский

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Alkylation of Glycine Derivatives through a Synergistic Single-Electron Transfer and Halogen-Atom Transfer Process

Organic Letters, Journal Year: 2024, Volume and Issue: 26(36), P. 7507 - 7513

Published: Aug. 29, 2024

Here, we present a versatile method for forming C(sp

Language: Английский

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Solvent- and additive-free oxidative amidation of aldehydes using a recyclable oxoammonium salt

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(11), P. 2249 - 2254

Published: Jan. 1, 2022

A solvent- and additive-free oxidative functionalisation approach to prepare acyl azoles from aldehydes mediated by a substoichiometric quantity of recyclable oxoammonium salt.

Language: Английский

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Chemodivergent Synthesis of Indeno[1,2-b]indoles and Isoindolo[2,1-a]indoles via Mn(III)-Mediated or Electrochemical Intramolecular Radical Cross-Dehydrogenative Coupling

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(16), P. 10967 - 10981

Published: July 28, 2022

Chemodivergent synthesis of indeno[1,2-b]indoles and isoindolo[2,1-a]indoles from the same starting materials involving radical cross-dehydrogenative couplings have been developed. Mn(OAc)3·2H2O selectively promoted an intramolecular C–H/C–H dehydrogenative coupling reaction to provide indeno[1,2-b]indoles, while C–H/N–H could proceed via electrochemistry deliver isoindolo[2,1-a]indoles. Plausible mechanisms chemodivergent reactions were proposed.

Language: Английский

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