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Volumn 74, Issue 1, 2009, Pages 289-297

Application of secondary alkyl halides to a domino aryl alkylation reaction for the synthesis of aromatic heterocycles

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL HALIDES; ALKYLATION REACTIONS; ARYL IODIDES; CATALYZED REACTIONS; CHEMICAL EQUATIONS; DOMINO PROCESSES; HETEROCYCLES; NITROGEN BONDS; NORBORNENE; ONE POTS; SYNTHESIS OF;

EID: 58149311070     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802180h     Document Type: Article
Times cited : (58)

References (75)
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    • Dyker, G, Ed, Wiley-VCH: Weinheim
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    • (2005) Handbook of C-H Transformations
  • 30
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    • For selected examples with the Heck reaction, see: a
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  • 34
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    • With direct arylation, see: (e) Bressy, C, Alberico, D, Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148-13149
    • With direct arylation, see: (e) Bressy, C.; Alberico, D.; Lautens, M. J. Am. Chem. Soc. 2005, 127, 13148-13149.
  • 37
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    • For reduction of the aryl halide bond, see: h
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    • Wilhelm, T.1    Lautens, M.2
  • 40
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    • GC yield based on the amount of charged aryl iodide
    • GC yield based on the amount of charged aryl iodide.
  • 43
    • 58149296629 scopus 로고    scopus 로고
    • In the presence of an external Heck acceptor, coordination of norbornene to intermediate 2 is preferred due to the steric strain relief associated with carbopalladation to form intermediate 3. While norbornene is theoretically required in catalytic amounts, often stoichiometric quantities are used to moderate the competitive reactions in the system, namely direct Heck reaction of intermediate 2. For further information, see ref 12d
    • In the presence of an external Heck acceptor, coordination of norbornene to intermediate 2 is preferred due to the steric strain relief associated with carbopalladation to form intermediate 3. While norbornene is theoretically required in catalytic amounts, often stoichiometric quantities are used to moderate the competitive reactions in the system, namely direct Heck reaction of intermediate 2. For further information, see ref 12d.
  • 45
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    • (2007) Chem. Rev , vol.107 , pp. 174-238
    • Alberico, D.1    Scott, M.E.2    Lautens, M.3
  • 55
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    • Previous studies by Catellani on palladacycle formation with analogous 1-iodo-3-methoxybenzene show that reaction at the C-H bond next to the methoxy group is preferred, see: (a) Catellani, M.; Chiusoli, G. P.; Ricotti, S. J. Organomet. Chem. 1985, 296, C11-C15.
    • Previous studies by Catellani on palladacycle formation with analogous 1-iodo-3-methoxybenzene show that reaction at the C-H bond next to the methoxy group is preferred, see: (a) Catellani, M.; Chiusoli, G. P.; Ricotti, S. J. Organomet. Chem. 1985, 296, C11-C15.
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    • For a review of oxidative addition and reductive elimination, including stereochemical issues regarding Pd(II)-Pd(IV) intermediates, see: (a) Stille, J. K. The Chemistry of the Metal-Carbon Bond; 2; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Chapter 9.
    • For a review of oxidative addition and reductive elimination, including stereochemical issues regarding Pd(II)-Pd(IV) intermediates, see: (a) Stille, J. K. The Chemistry of the Metal-Carbon Bond; Vol. 2; Hartley, F. R., Patai, S., Eds.; Wiley: New York, 1985; Chapter 9.
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    • N2 vs. direct insertion pathways of oxidative addition, see: (a) Collman, J. P.; Hegedus, L. S. L. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; Chapter 4.
    • N2 vs. direct insertion pathways of oxidative addition, see: (a) Collman, J. P.; Hegedus, L. S. L. Principles and Applications of Organotransition Metal Chemistry; University Science Books: Mill Valley, CA, 1980; Chapter 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.