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Volumn 10, Issue 13, 2008, Pages 2697-2700

Copper(I)-catalyzed carboxylation of aryl- and alkenylboronic esters

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EID: 56449084526     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol800829q     Document Type: Article
Times cited : (222)

References (52)
  • 1
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    • 2-fixation reactions, see: (a) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747.
    • 2-fixation reactions, see: (a) Braunstein, P.; Matt, D.; Nobel, D. Chem. Rev. 1988, 88, 747.
  • 5
    • 0030990529 scopus 로고    scopus 로고
    • For recent examples of catalytic nucleophilic addition of carbonucleophiles containing a carbon, transition metal bond toward CO 2, see: (a) Shi, M, Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 5057
    • 2, see: (a) Shi, M.; Nicholas, K. M. J. Am. Chem. Soc. 1997, 119, 5057.
  • 12
    • 3242808098 scopus 로고    scopus 로고
    • For reactions of boronate reagents with copper(I) complexes including the transmetalation step, see: (a) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
    • For reactions of boronate reagents with copper(I) complexes including the transmetalation step, see: (a) Wada, R.; Oisaki, K.; Kanai, M.; Shibasaki, M. J. Am. Chem. Soc. 2004, 126, 8910.
  • 24
    • 37049087361 scopus 로고
    • For catalytic carboxylation reactions with carbon dioxide with copper catalyst see: a
    • For catalytic carboxylation reactions with carbon dioxide with copper catalyst see: (a) Fukue, Y.; Oi, S.; Inoue, Y. J. Chem. Soc., Chem. Commun. 1994, 2091.
    • (1994) J. Chem. Soc., Chem. Commun , pp. 2091
    • Fukue, Y.1    Oi, S.2    Inoue, Y.3
  • 27
    • 59949101990 scopus 로고    scopus 로고
    • This work was partly presented in the 88th Annual Meeting of Chemical Society of Japan, March 2008, 2H332. An analogous copper-catalyzed carboxylation of aryl- or alkenylboronic esters with CO2 was reported by Prof. Hou's group at the same meeting. See: Ohishi, T, Hou, Z. The 88th Annual Meeting of Chemical Society of Japan, March 2008, 2H333. We would like to thank Prof. Hou for discussion on this subject
    • 2 was reported by Prof. Hou's group at the same meeting. See: Ohishi, T.; Hou, Z. The 88th Annual Meeting of Chemical Society of Japan, March 2008, 2H333. We would like to thank Prof. Hou for discussion on this subject.
  • 28
    • 59949100275 scopus 로고    scopus 로고
    • The active catalyst seemed to be sensitive to water and oxygen in the air and decrease of the yield of carboxylation product was often observed in the reaction under 1 atm CO2 with a balloon. A closed system can achieve good reproducibility
    • 2 with a balloon. A closed system can achieve good reproducibility.
  • 29
    • 59949087976 scopus 로고    scopus 로고
    • Other solvent such as toluene, 1,4-dioxane, and acetonitrile resulted in low conversion and only a trace amount of carboxylation product was obtained
    • Other solvent such as toluene, 1,4-dioxane, and acetonitrile resulted in low conversion and only a trace amount of carboxylation product was obtained.
  • 30
    • 0025042702 scopus 로고
    • For reactions of bisoxazoline-Cu catalyst, see: a
    • For reactions of bisoxazoline-Cu catalyst, see: (a) Lowenthal, R. E.; Abiko, A.; Masamune, S. Tetrahedron Lett. 1990, 31, 6005.
    • (1990) Tetrahedron Lett , vol.31 , pp. 6005
    • Lowenthal, R.E.1    Abiko, A.2    Masamune, S.3
  • 35
    • 59949085377 scopus 로고    scopus 로고
    • Generality of the reaction was examined with 5 mol % of CuI at 90 °C to shorten the reaction time.
    • Generality of the reaction was examined with 5 mol % of CuI at 90 °C to shorten the reaction time.
  • 44
    • 0037059546 scopus 로고    scopus 로고
    • Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III Science 2002, 295, 305.
    • (c) Cho, J.-Y.; Tse, M. K.; Holmes, D.; Maleczka, R. E., Jr.; Smith, M. R., III Science 2002, 295, 305.
  • 51
    • 33845457554 scopus 로고    scopus 로고
    • Paul, S.; Chotana, G. A.; Holmes, D.; Reichle, R. C.; Maleczka, R. E., Jr.; Smith, M. R., III J. Am. Chem. Soc. 2006, 128, 15552.
    • (j) Paul, S.; Chotana, G. A.; Holmes, D.; Reichle, R. C.; Maleczka, R. E., Jr.; Smith, M. R., III J. Am. Chem. Soc. 2006, 128, 15552.
  • 52
    • 59949099800 scopus 로고    scopus 로고
    • The reaction did not proceed without CsF. Concerning the effect of CsF, promotion of the transmetalation step by forming arylfluoroborates would be most likely although participation in the carboxylation step by making fluorocuprate might also be possible. Research is now in progress to elucidate the mechanism including the role of CsF and also of the oxazoline ligand
    • The reaction did not proceed without CsF. Concerning the effect of CsF, promotion of the transmetalation step by forming arylfluoroborates would be most likely although participation in the carboxylation step by making fluorocuprate might also be possible. Research is now in progress to elucidate the mechanism including the role of CsF and also of the oxazoline ligand.


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