Palladium-catalyzed regio- and chemoselective ortho-benzylation of C-H bond using a functionalizable primary amide directing group: a concise synthesis of dibenzo[b,e]azepin-6-ones.
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Summary
A palladium-catalyzed regio- and chemoselective direct benzylation of primary benzamides with 2-bromobenzyl bromides under a mild basic condition has been developed affording various substituted diarylmethanes in good yields.
- Type
- article
- Published
- 2013-08-01
- Cited by
- 33
- References
- 35
- OpenAlex
- https://openalex.org/W23873087
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:5460818
Keywords
Afterglow, Impurity, Metastability, Spectrograph, Atomic physics
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- 11-Alkoxy-dibenzo[b,e]azepin-6-ones with anti-convulsant activity
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- Direct Pd-catalyzed benzylation of highly electron-deficient perfluoroarenes.
- Transition-Metal-Catalyzed Direct C–H Alkenylation, Alkynylation, Benzylation, and Alkylation of (Hetero)arenes
Cited by
- Unsymmetrical Diarylmethanes by Ferroceniumboronic Acid Catalyzed Direct Friedel-Crafts Reactions with Deactivated Benzylic Alcohols: Enhanced Reactivity due to Ion-Pairing Effects.
- Dual Catalysis in Domino N‐Benzylation/Intramolecular C–H Arylation: Regio‐ and Chemoselective Synthesis of Annelated Nitrogen Heterocycles
- Mechanistic Insights into the Palladium‐Catalyzed Domino Synthesis of 10,11‐Dihydro‐5H‐dibenzo[b,e][1,4]diazepines
- Palladium-catalyzed regiocontrolled domino synthesis of N-sulfonyl dihydrophenanthridines and dihydrodibenzo[c,e]azepines: control over the formation of biaryl sultams in the intramolecular direct arylation.
- Recent advances in copper-catalyzed C–H bond amidation
- Implications of dynamic imine chemistry for the sustainable synthesis of nitrogen heterocycles via transimination followed by intramolecular cyclisation.
- Access to biaryl sulfonamides by palladium-catalyzed intramolecular oxidative coupling and subsequent nucleophilic ring opening of heterobiaryl sultams with amines.
- Palladium-catalyzed intramolecular oxidative coupling involving double C(sp(2))-H bonds for the synthesis of annulated biaryl sultams.
- Sulfate Radical Anion (SO4(•-)) Mediated C(sp(3))-H Nitrogenation/Oxygenation in N-Aryl Benzylic Amines Expanded the Scope for the Synthesis of Benzamidine/Oxazine Heterocycles.
- The Friedel-Crafts Benzylation of Arenes and the Synthesis of Sterically Hindered Amides
- Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions
- Primary Amide Directed Regioselective ortho-C-H-Arylation of (Aryl)Acetamides.
- Multiple Aryne Insertions into Oxindoles: Synthesis of Bioactive 3,3-Diarylated Oxindoles and Dibenzo[b,e]azepin-6-ones.
- Synthesis of 5H-Dibenzo[c,e]azepine-5,7(6H)-diones from Benzamides via Palladium-Catalyzed Double C-H Bond Activation.
- Geometry Driven Intramolecular Oxidative Cyclization of Enamides: An Umpolung Annulation of Primary Benzamides with Acrylates for the Synthesis of 3-Methyleneisoindolin-1-ones.
- Palladium-Catalyzed Decarboxylative Ortho-Acylation of Tertiary Benzamides with Arylglyoxylic Acids
- Efficient synthesis of benzene-fused 6/7-membered amides via Xphos Pd G2 catalyzed intramolecular C–N bond formation
- Nickel-Catalyzed Cross-Dehydrogenative Coupling of α-C(sp3)-H Bonds in N-Methylamides with C(sp3)-H Bonds in Cyclic Alkanes.
- Dibenzo[b,e]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intramolecular Heck Reaction and Application towards Drug-Like Small Molecules
- A Modular Approach to Dibenzo-fused ε-Lactams: Palladium Carbene Bridging C-H Activation and Its Synthetic Application.
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