- Delineating ligand effects in intramolecular aryl amidation reactions: formation of a novel spiro-heterocycle by a tandem cyclisation process
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Ligand effects for intramolecular Pd-catalysed aryl amidation reaction were examined for the synthesis of seven-membered benzolactam rings. In an attempt to produce an eight-membered ring, tandem C-N/C-O bond forming reactions occurred to give a novel spi
- Cropper, Emma L.,Yuen, Aui-Ping,Ford, Agnes,White, Andrew J.P.,(Mimi) Hii, King Kuok
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experimental part
p. 525 - 530
(2009/04/07)
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- Synthesis of novel phenylnaphthyl phosphines and their applications to Pd-catalyzed intramolecular amidation
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Novel phenylnaphthyl phosphines were prepared and applied to the Pd-catalyzed intramolecular amidation. Both ligands gave good to excellent yields in the synthesis of five-, six-, and seven-membered rings from halo-amides and carbamates. Georg Thieme Verl
- Kitamura, Yuki,Hashimoto, Ayano,Yoshikawa, Seiji,Odaira, Jun-Ichi,Furuta, Takumi,Kan, Toshiyuki,Tanaka, Kiyoshi
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p. 115 - 117
(2007/10/03)
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- The development of efficient protocols for the palladium-catalyzed cyclization reactions of secondary amides and carbamates
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(equation presented) With the proper choice of palladium catalyst, ligand, and base, five-, six-, and seven-membered rings are formed efficiently from secondary amide or secondary carbamate precursors, offering significant improvements to currently existing methodology.
- Yang, Bryant H.,Buchwald, Stephen L.
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- Intramolecular palladium-catalyzed aryl amination and aryl amidation
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Upon treatment with a palladium catalyst and a suitable base, aromatic halides undergo intramolecular substitution to form five, six, and seven-membered rings. In a similar fashion aryl halides with pendant amides or sulfonamides are cyclized to form five and six-membered rings.
- Wolfe, John P.,Rennels, Roger A.,Buchwald, Stephen L.
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p. 7525 - 7546
(2007/10/03)
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- Aryl radical cyclisations: Quinoline, isoquinolone, and 1-benzazepin-2-one rings via 6- and 7-exo cyclisations
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The cyclisation of aryl radicals derived by treatment of aryl halides (1a), (1b), (4), (7a), (7b), and (10) with tri-n-butyltin hydride has been investigated.
- Clark,Jones,McCarthy,Storey
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p. 2829 - 2832
(2007/10/02)
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- Photochemistry of 2'-substituted 1,2,3,4-Tetrahydronaphthalene-1-spiro-3'-oxaziridines. Variable-temperature 1H Nuclear Magnetic Resonance Spectroscopy of 1-Substituted 1,3,4,5-Tetrahydro-2H-1-benzazepin-2-ones
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The lack of regioselectivity of photorearrangement of the title spiro-oxaziridines in wich the N-substituent is syn to the aromatic ring suggests that the first formed N-O-bond-cleaved species has a significant lifetime allowing rotation (inversion) to complete with rearrangement.The energy barrier to ring inversion of the title tetrahydro-1-benzazepin-2-ones is significantly influenced by the steric interaction between the N-substituent and the peri hydrogen atom.
- Johnson, Graham P.,Marples, Brian A.
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p. 3399 - 3406
(2007/10/02)
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- PHOTOCHEMISTRY OF N-SUBSTITUTED SPIROOXAZIRIDINES DERIVED FROM TETRALONE-1
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Photolyses of spirooxaziridines from tetralone-1 in which the N-substituent is syn to the aromatic ring are less regioselective than their anti-isomers suggesting the first formed N-O bond cleaved species has a significant life time.
- Johnson, G. P.,Marples, B. A.
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p. 3359 - 3362
(2007/10/02)
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