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Volumn 131, Issue 11, 2009, Pages 4031-4041

Modular synthesis of indoles from imines and o-dihaloarenes or o-chlorosulfonates by a Pd-catalyzed cascade process

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC HYDROCARBONS; NITROGEN COMPOUNDS; ORGANIC POLYMERS; PALLADIUM; PHENOLS; POSITIVE IONS; REACTION KINETICS;

EID: 67749120541     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja808652a     Document Type: Article
Times cited : (154)

References (78)
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    • A more detailed study on the arylation of imines, to provide an interesting synthetic methodology, will be published elsewere
    • A more detailed study on the arylation of imines, to provide an interesting synthetic methodology, will be published elsewere.
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    • The reaction of imine 1a with chlorotriflate 14 was examined with the following ligands: tricyclohexylphosphine, 2-dicyclohexylphos-phino-2́-(A,A-dimethylamino)biphenyl (Davephos), 4,5-bis(diphe-nylphosphino)-9,9-dimethylxanthene (Xantphos), and Josiphos. The following commercial complexes of Pd with N-heterocyclic carbenes were also tested: PEPPSI-IPr, PEPPSI-SIPr.
    • The reaction of imine 1a with chlorotriflate 14 was examined with the following ligands: tricyclohexylphosphine, 2-dicyclohexylphos-phino-2́-(A,A-dimethylamino)biphenyl (Davephos), 4,5-bis(diphe-nylphosphino)-9,9-dimethylxanthene (Xantphos), and Josiphos. The following commercial complexes of Pd with N-heterocyclic carbenes were also tested: PEPPSI-IPr, PEPPSI-SIPr.
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    • Slow addition had previously been employed in the original procedures for the amination of aryl triflates. See: (a) Louie, J, Driver, M. S, Hamann, B. C, Hartwig, J. F. J. Org. Chem. 1997, 62, 1268
    • Slow addition had previously been employed in the original procedures for the amination of aryl triflates. See: (a) Louie, J.; Driver, M. S.; Hamann, B. C.; Hartwig, J. F. J. Org. Chem. 1997, 62, 1268.
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    • The α-arylation of ketones with aryl triflates has recently been reported (see: Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195.), but to the best of our knowledge, aryl nonaflates have not previously been employed in a-arylation reactions.
    • The α-arylation of ketones with aryl triflates has recently been reported (see: Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195.), but to the best of our knowledge, aryl nonaflates have not previously been employed in a-arylation reactions.
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    • For a recent regioselective synthesis of 6-substituted indoles through the Neber rearrangement, see: (a) Taber, D. F.; Tian, W. J. Am. Chem. Soc. 2006, 128, 1058.
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    • For a regioselective synthesis of indoles from o-nitrohalobenzene derivatives, see:Rutherford, J. L.; Rainka, M. P.; Buchwald, S. L. J. Am. Chem. Soc. 2002, 124, 15168.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.