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Literature DB >> 22780559

Aromatic cations from oxidative carbon-hydrogen bond cleavage in bimolecular carbon-carbon bond forming reactions.

Abstract

Chromenes and isochromenes react quickly with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) to form persistent aromatic oxocarbenium ions through oxidative carbon-hydrogen cleavage. This process is tolerant of electron-donating and electron-withdrawing groups on the benzene ring and additional substitution on the pyran ring. A variety of nucleophiles can be added to these cations to generate a diverse set of structures.

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Year: 2012 PMID： 22780559 PMCID： PMC3432936 DOI： 10.1021/jo301185h

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.354

47 in total

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5. Nickel-catalyzed cross-coupling of chromene acetals and boronic acids.

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6. DDQ-mediated direct cross-dehydrogenative-coupling (CDC) between benzyl ethers and simple ketones.

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8. Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

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Aromatic cations from oxidative carbon-hydrogen bond cleavage in bimolecular carbon-carbon bond forming reactions.

Review 1. Design and implementation of new, silicon-based, cross-coupling reactions: importance of silicon-oxygen bonds.

2. A 'rule of three' for fragment-based lead discovery?

3. Facial-selective allylation of methyl ketones for the asymmetric synthesis of alpha-substituted tertiary homoallylic ethers.

4. C-H functionalization logic in total synthesis.

5. Nickel-catalyzed cross-coupling of chromene acetals and boronic acids.

6. DDQ-mediated direct cross-dehydrogenative-coupling (CDC) between benzyl ethers and simple ketones.

7. Enantioselective total synthesis of (-)-zampanolide, a potent microtubule-stabilizing agent.

8. Catalytic asymmetric α-acylation of tertiary amines mediated by a dual catalysis mode: N-heterocyclic carbene and photoredox catalysis.

Review 9. Stereoselective heterocycle synthesis through oxidative carbon-hydrogen bond activation.

10. Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.

1. Cyclopropane compatibility with oxidative carbocation formation: total synthesis of clavosolide A.

2. Bimolecular Coupling Reactions through Oxidatively Generated Aromatic Cations: Scope and Stereocontrol.

3. Copper-catalyzed oxidative cross-dehydrogenative coupling of 2H-chromenes and terminal alkynes.

4. Remodeling of fumagillol: discovery of an oxygen-directed oxidative Mannich reaction.

5. Kinetic resolution in asymmetric epoxidation using iminium salt catalysis.