메뉴 건너뛰기




Volumn 10, Issue 5, 2008, Pages 1033-1035

Iridium-catalyzed C-C coupling via transfer hydrogenation: Carbonyl addition from the alcohol or aldehyde oxidation level employing 1,3-cyclohexadiene

Author keywords

[No Author keywords available]

Indexed keywords

1,3 CYCLOHEXADIENE; 1,3-CYCLOHEXADIENE; ALCOHOL DERIVATIVE; ALDEHYDE; CYCLOHEXENE DERIVATIVE; IRIDIUM; KETONE;

EID: 43549090940     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800159w     Document Type: Article
Times cited : (101)

References (45)
  • 1
    • 33846995439 scopus 로고    scopus 로고
    • For reviews on hydrogenative C-C coupling, see: a
    • For reviews on hydrogenative C-C coupling, see: (a) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
    • (2007) J. Org. Chem , vol.72 , pp. 1063
    • Ngai, M.-Y.1    Kong, J.-R.2    Krische, M.J.3
  • 4
    • 31444453628 scopus 로고    scopus 로고
    • For recent examples, see: (a) C=X Vinylation: Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718
    • For recent examples, see: (a) C=X Vinylation: Kong, J.-R.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2006, 128, 718
  • 5
    • 58149193804 scopus 로고    scopus 로고
    • Skucas, E.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2007, 729, 7242. (c) Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432.
    • (b) Skucas, E.; Kong, J.-R.; Krische, M. J. J. Am. Chem. Soc. 2007, 729, 7242. (c) Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 129, 8432.
  • 6
    • 58149182852 scopus 로고    scopus 로고
    • Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 729, 12644. Aldol and Mannich addition: Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
    • Barchuk, A.; Ngai, M.-Y.; Krische, M. J. J. Am. Chem. Soc. 2007, 729, 12644. Aldol and Mannich addition: Jung, C.-K.; Garner, S. A.; Krische, M. J. Org. Lett. 2006, 8, 519.
  • 9
    • 58149180540 scopus 로고    scopus 로고
    • Bee, C; Iida, H.; Han, S. B.; Hassan, A.; Krische, M. J. J. Am. Chem. Soc. 2008, 130. In Press, (h) C=O Allylation: Skucas, E.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2007, 729, 12678.
    • (g) Bee, C; Iida, H.; Han, S. B.; Hassan, A.; Krische, M. J. J. Am. Chem. Soc. 2008, 130. In Press, (h) C=O Allylation: Skucas, E.; Bower, J. F.; Krische, M. J. J. Am. Chem. Soc. 2007, 729, 12678.
  • 11
    • 34250893845 scopus 로고    scopus 로고
    • For reviews on hydrogen autotransl'er, see: a
    • For reviews on hydrogen autotransl'er, see: (a) Guillena. G.; Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2007, 46, 2358.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 2358
    • Guillena, G.1    Ramón, D.J.2    Yus, M.3
  • 13
    • 58149180538 scopus 로고    scopus 로고
    • Withstanding work cited in refs 2i and 5, reported hydrogen autotransfer processes involve three fundamental steps: (i) alcohol oxidation, ii) carbonyl condensation/olefination, iii) olefin reduction to deliver saturated products
    • Withstanding work cited in refs 2i and 5, reported hydrogen autotransfer processes involve three fundamental steps: (i) alcohol oxidation, (ii) carbonyl condensation/olefination, (iii) olefin reduction to deliver saturated products.
  • 14
    • 34249778089 scopus 로고    scopus 로고
    • Aryl amine-olefin hydrogen autotransfer provides products of inline addition from the amine oxidation level, see: Herzon, S. B, Hartwig. J. F. J. Am. Chem. Soc. 2007, 129, 6690 and references cited therein
    • Aryl amine-olefin hydrogen autotransfer provides products of inline addition from the amine oxidation level, see: Herzon, S. B.; Hartwig. J. F. J. Am. Chem. Soc. 2007, 129, 6690 and references cited therein.
  • 15
    • 40149091315 scopus 로고    scopus 로고
    • For a three-component Ni-catalyzed C-C coupling involving internal redox, see
    • For a three-component Ni-catalyzed C-C coupling involving internal redox, see: Herath, A.; Li. W.; Montgomery, J. J. Am. Chem. Soc. 2008, 130, 469.
    • (2008) Am. Chem. Soc , vol.130 , pp. 469
    • Herath, A.1    Li, W.2    Montgomery, J.J.3
  • 16
    • 36448968256 scopus 로고    scopus 로고
    • For an example of catalytic metal-hydride mediated C-C coupling using isopropanol as a hydride donor, see: Gligorich, K. M, Cummings. S. A, Sigman. M. S. J. Am. Chem. Soc. 2007, 129, 14193
    • For an example of catalytic metal-hydride mediated C-C coupling using isopropanol as a hydride donor, see: Gligorich, K. M.; Cummings. S. A.; Sigman. M. S. J. Am. Chem. Soc. 2007, 129, 14193.
  • 17
    • 0010456977 scopus 로고    scopus 로고
    • Catalytic intramolecular diene-aldehyde reductive coupling: (a) Sato, Y.; Takimoto. M.; Hayashi, K.; Katsuhara, T.; Takagi, JC; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
    • Catalytic intramolecular diene-aldehyde reductive coupling: (a) Sato, Y.; Takimoto. M.; Hayashi, K.; Katsuhara, T.; Takagi, JC; Mori, M. J. Am. Chem. Soc. 1994, 116, 9771.
  • 26
    • 58149181948 scopus 로고    scopus 로고
    • Catalytic intermolecular diene-aldehyde reductive coupling: (a) Kimura, M.; Ezoe, A.: Shibata. K.; Tamaru. Y. J. Am. Chem. Soc. 1998, 120, 4033.
    • Catalytic intermolecular diene-aldehyde reductive coupling: (a) Kimura, M.; Ezoe, A.: Shibata. K.; Tamaru. Y. J. Am. Chem. Soc. 1998, 120, 4033.
  • 38
    • 0001374863 scopus 로고    scopus 로고
    • For reviews encompassing nickel-catalyzed diene-aldehyde reductive coupling, see: a
    • For reviews encompassing nickel-catalyzed diene-aldehyde reductive coupling, see: (a) Tamaru, Y. J. Organomet. Chem. 1999, 576, 215.
    • (1999) J. Organomet. Chem , vol.576 , pp. 215
    • Tamaru, Y.1
  • 41
    • 58149182851 scopus 로고    scopus 로고
    • Tamaru, Y, Ed, Wiley-VCH: Weinheim, Germany
    • (d) Tamaru, Y, Ed. Modem Organo Nickel Chemistry, Wiley-VCH: Weinheim, Germany, 2005.
    • (2005) Modem Organo Nickel Chemistry
  • 43
    • 58149188450 scopus 로고    scopus 로고
    • The stereochemical assignment of lc was made by comparison with the corresponding literature NMR data.9j The stereochemical assignment of products 2c-9c was made in analogy to lc. That lc and 1d are regioisomers (and not diastcrcomers) was confirmed by oxidation (DessMartin periodinane) to the corresponding mixture of ketones and comparison with relevant literature NMR data. See Supporting Information for details
    • 9j The stereochemical assignment of products 2c-9c was made in analogy to lc. That lc and 1d are regioisomers (and not diastcrcomers) was confirmed by oxidation (DessMartin periodinane) to the corresponding mixture of ketones and comparison with relevant literature NMR data. See Supporting Information for details.
  • 44
    • 0037016413 scopus 로고    scopus 로고
    • 4NI additive is unclear. For a review on the effect of halide additives in metal-catalvzed reactions, see: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26.
    • 4NI additive is unclear. For a review on the effect of halide additives in metal-catalvzed reactions, see: Fagnou, K.; Lautens, M. Angew. Chem., Int. Ed. 2002, 41, 26.
  • 45
    • 58149200140 scopus 로고    scopus 로고
    • In the absence of isopropanol, benzaldehyde lb is converted to lc in 5% yield
    • In the absence of isopropanol, benzaldehyde lb is converted to lc in 5% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.