Palladium-catalyzed highly selective ortho-halogenation (I, Br, Cl) of arylnitriles via sp2 C-H bond activation using cyano as directing group.
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Summary
A palladium-catalyzed ortho-halogenation of arylnitrile using cyano as the directing group gave good to excellent yields and was successfully applied to the synthesis of the precursors of paucifloral F and isopaucifloreal F.
- Type
- article
- Published
- 2013-02-11
- Cited by
- 107
- References
- 44
- Access
- Open access
- OpenAlex
- https://openalex.org/W23373558
- Semantic Scholar
- https://api.semanticscholar.org/CorpusID:207247449
Keywords
Computer science
References
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- Palladium-catalyzed aromatic C-H halogenation with hydrogen halides by means of electrochemical oxidation.
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- Pd-catalyzed oxidative coupling with organometallic reagents via C-H activation.
- Book review: Metal-catalyzed cross-coupling reactions. F. Diederich and P. J. Stang (eds) Wiley–VCH, Weinheim, 1998. xxi + 517 pages, £85 ISBN 3–527–29421–X
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- Pd(OAc)2-catalyzed alkoxylation of arylnitriles via sp2 C-H bond activation using cyano as the directing group.
- A simple catalytic method for the regioselective halogenation of arenes.
- Expedient drug synthesis and diversification via ortho-C-H iodination using recyclable PdI2 as the precatalyst.
- Pd(II)-catalyzed hydroxylation of arenes with 1 atm of O(2) or air.
Cited by
- Palladium(II)/N-Heterocyclic Carbene-Catalyzed Direct C-H Acylation of Heteroarenes with N-Acylsaccharins.
- Chlorination of (Phebox)Ir(mesityl)(OAc) by Thionyl Chloride
- Facile, One‐Pot, and Gram‐Scale Synthesis of 3,4,5‐Triiodoanisole through a C–H Iodination/ipso‐Iododecarboxylation Strategy: Potential Application towards 3,4,5‐Trisubstituted Anisoles
- Iridium-catalyzed silylation of aryl C-H bonds.
- Ruthenium-catalyzed ortho alkenylation of aromatic nitriles with activated alkenes via C-H bond activation.
- Metal catalyzed defunctionalization reactions.
- Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups
- Nitrogen Dioxide-Catalyzed Electrophilic Iodination of Arenes
- Palladium N-heterocyclic carbene catalyzed regioselective C–H halogenation of 1-aryl-3-methyl-1H-pyrazol-5(4H)-ones using N-halosuccinimides (NXS)
- Palladium-catalyzed alkenylation via sp2 C-H bond activation using phenolic hydroxyl as the directing group.
- Pd(II)-catalyzed aminotetrazole-directed ortho-selective halogenation of arenes.
- Metal‐Free Directed ortho C–H Iodination: Synthesis of 2′‐Iodobiaryl‐2‐carbonitriles
- Nickel-catalyzed hydrogenolysis of unactivated carbon-cyano bonds.
- Palladium catalyzed ortho-halogenation of 2-arylbenzothiazole and 2,3-diarylquinoxaline
- Recent advances in directed C–H functionalizations using monodentate nitrogen-based directing groups
- Transition-metal-catalyzed π-bond-assisted C - H bond functionalization: an emerging trend in organic synthesis.
- Ester‐Directed Selective Olefination of Acrylates by Rhodium Catalysis
- Directing-group-assisted copper-catalyzed oxidative esterification of phenols with aldehydes.
- Synthesis of Diiodinated Biphenyls and Iodinated meta-Terphenyls by Regioselective Suzuki–Miyaura Cross-Coupling Reactions of 5-Substituted 1,2,3-Triiodobenzenes
- The regioselective iodination of quinolines, quinolones, pyridones, pyridines and uracil.
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