메뉴 건너뛰기




Volumn 351, Issue 7-8, 2009, Pages 1101-1114

Synthesis of fluorenes via the palladium-catalyzed 5-exo-dig annulation of o-alkynylbiaryls

Author keywords

Alkynes; Annulations; Arylation; C H activation; Palladium

Indexed keywords


EID: 66149097349     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200800765     Document Type: Article
Times cited : (76)

References (79)
  • 1
    • 2342572058 scopus 로고    scopus 로고
    • For recent reviews on palladium-catalyzed annulation reactions in organic synthesis, see, for example: a, Eds, E. Negishi, A. de Meijere, Willey-Interscience, New York
    • For recent reviews on palladium-catalyzed annulation reactions in organic synthesis, see, for example: a) S. Brase, A. de Meijere, in: Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1, (Eds.: E. Negishi, A. de Meijere), Willey-Interscience, New York, 2002, pp 1369-1403;
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.1 , pp. 1369-1403
    • Brase, S.1    de Meijere, A.2
  • 6
    • 51049114031 scopus 로고    scopus 로고
    • For recent reviews on annulation reactions catalyzed by π-philic metals, see: a
    • For recent reviews on annulation reactions catalyzed by π-philic metals, see: a) N. T. Patil, Y. Yamamoto, Chem. Rev. 2008, 108, 3395-3442;
    • (2008) Chem. Rev , vol.108 , pp. 3395-3442
    • Patil, N.T.1    Yamamoto, Y.2
  • 9
    • 51249100498 scopus 로고    scopus 로고
    • d) A. Arcadi, Chem. Rev. 2008, 108, 3266-3325;
    • (2008) Chem. Rev , vol.108 , pp. 3266-3325
    • Arcadi, A.1
  • 14
    • 13844250379 scopus 로고    scopus 로고
    • For a review on transition metal-catalyzed hydroaryla-tion of alkynes, see: a
    • For a review on transition metal-catalyzed hydroaryla-tion of alkynes, see: a) C. Nevado, A. M. Echavarren, Synthesis 2005, 167-182.
    • (2005) Synthesis , pp. 167-182
    • Nevado, C.1    Echavarren, A.M.2
  • 15
    • 4744342870 scopus 로고    scopus 로고
    • For recent Pt- and Au-catalyzed hydroarylations of alkynes, see: b
    • For recent Pt- and Au-catalyzed hydroarylations of alkynes, see: b) V. Mamane, P. Hannen, A. Fiirstner, Chem. Eur. J. 2004, 10, 4556-4575;
    • (2004) Chem. Eur. J , vol.10 , pp. 4556-4575
    • Mamane, V.1    Hannen, P.2    Fiirstner, A.3
  • 20
    • 3342973109 scopus 로고    scopus 로고
    • For other selected examples of Pd-catalyzed hydroary-lation of alkynes, see: a
    • For other selected examples of Pd-catalyzed hydroary-lation of alkynes, see: a) M. S. Viciu, E. D. Stevens, J. L. Petersen, S. P. Nolan, Organometallics 2004, 23, 3752-3755;
    • (2004) Organometallics , vol.23 , pp. 3752-3755
    • Viciu, M.S.1    Stevens, E.D.2    Petersen, J.L.3    Nolan, S.P.4
  • 22
    • 0034699309 scopus 로고    scopus 로고
    • For an intermolecular version of this reaction, see: c
    • For an intermolecular version of this reaction, see: c) W. Lu, C. Jia, T. Kitamura, Y. Fujiwara, Org. Lett. 2000, 2, 2927-2930.
    • (2000) Org. Lett , vol.2 , pp. 2927-2930
    • Lu, W.1    Jia, C.2    Kitamura, T.3    Fujiwara, Y.4
  • 26
    • 66149123848 scopus 로고    scopus 로고
    • It was assumed that the geometry of all geometrically pure products was the same as those for 2e, f, the geometries of which were confirmed by NOESY. experiments.
    • It was assumed that the geometry of all geometrically pure products was the same as those for 2e, f, the geometries of which were confirmed by NOESY. experiments.
  • 27
    • 0037694384 scopus 로고    scopus 로고
    • It is not clear whether this isomerization occurrs thermally, or it is assisted by Pd. For the Pd-assisted iso-merizations of alkenes, see, for example:, Eds, E. Negishi, A. de Meijere, Willey-Interscience, New York
    • It is not clear whether this isomerization occurrs thermally, or it is assisted by Pd. For the Pd-assisted iso-merizations of alkenes, see, for example: E. Negishi, in: Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 2, (Eds.: E. Negishi, A. de Meijere), Willey-Interscience, New York, 2002, pp 2783-2788.
    • (2002) Handbook of Organopalladium Chemistry for Organic Synthesis , vol.2 , pp. 2783-2788
    • Negishi, E.1
  • 28
    • 34249793676 scopus 로고    scopus 로고
    • For a discussion of kinetic isotope effects in palladium-catalyzed C-H activation processes, see, for example: a D. Garc4iAa-Cuadrado, P. de Mendoza, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2007, 129, 6880-6886;
    • For a discussion of kinetic isotope effects in palladium-catalyzed C-H activation processes, see, for example: a) D. Garc4iAa-Cuadrado, P. de Mendoza, A. A. C. Braga, F. Maseras, A. M. Echavarren, J. Am. Chem. Soc. 2007, 129, 6880-6886;
  • 37
    • 66149101115 scopus 로고    scopus 로고
    • Intramolecular hydroarylation of 3 produced fluorene 4 in 85% yield with 60% of deuterium incorporated at the vinylic position.
    • Intramolecular hydroarylation of 3 produced fluorene 4 in 85% yield with 60% of deuterium incorporated at the vinylic position.
  • 38
    • 0001748330 scopus 로고    scopus 로고
    • and references therein
    • R. C. Larock, Pure Appl. Chem. 1999, 71, 1435-1442, and references therein.
    • (1999) Pure Appl. Chem , vol.71 , pp. 1435-1442
    • Larock, R.C.1
  • 40
    • 0001375982 scopus 로고    scopus 로고
    • R. C. Larock, M. J. Dotty, Q. Tian, J. M. Zenner, J. Org. Chem. 1997, 62, 7536-7437;
    • b) R. C. Larock, M. J. Dotty, Q. Tian, J. M. Zenner, J. Org. Chem. 1997, 62, 7536-7437;
  • 45
    • 66149099837 scopus 로고    scopus 로고
    • For the regioselectivity of Pd-catalyzed arylations of triple bonds, see, for example: a S. Cacci, G. Fabrizi, in: Handbook of Organopalladium Chemistry for Organic Synthesis, 1, (Eds.: E. Negishi, A. de Meijere), Wiley-Interscience, New York, 2002, pp 1335-1367;
    • For the regioselectivity of Pd-catalyzed arylations of triple bonds, see, for example: a) S. Cacci, G. Fabrizi, in: Handbook of Organopalladium Chemistry for Organic Synthesis, Vol. 1, (Eds.: E. Negishi, A. de Meijere), Wiley-Interscience, New York, 2002, pp 1335-1367;
  • 48
    • 0001075641 scopus 로고    scopus 로고
    • R. C. Larock, J. Organomet. Chem. 1999, 576, 111-124.
    • d) R. C. Larock, J. Organomet. Chem. 1999, 576, 111-124.
  • 56
    • 45549107152 scopus 로고    scopus 로고
    • For a C=C triple bond serving as a directing group, together with an amide group, see: S. T. Peng., S.-F. Pi, Y. Liang, N.-X. Wang, J.-H. Li, Org. Lett. 2008, 10, 1179-1182.
    • For a C=C triple bond serving as a directing group, together with an amide group, see: S. T. Peng., S.-F. Pi, Y. Liang, N.-X. Wang, J.-H. Li, Org. Lett. 2008, 10, 1179-1182.
  • 57
    • 33744928374 scopus 로고    scopus 로고
    • Although coordination of ArPdX to a triple bond is a requisite step in numerous transformations, to the best of our knowledge, there are no reports on employment of the triple bond as a directing group in the Pd-cata-lyzed C-H arylation reactions. For use of other directing groups in C-H functionalizations, see, for example: pyridines: a K. L. Hull, W. Q. Anani, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 7134-7135;
    • Although coordination of ArPdX to a triple bond is a requisite step in numerous transformations, to the best of our knowledge, there are no reports on employment of the triple bond as a directing group in the Pd-cata-lyzed C-H arylation reactions. For use of other directing groups in C-H functionalizations, see, for example: pyridines: a) K. L. Hull, W. Q. Anani, M. S. Sanford, J. Am. Chem. Soc. 2006, 128, 7134-7135;
  • 60
    • 34249056813 scopus 로고    scopus 로고
    • amides: d S. Yang, B. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 6066-6067;
    • amides: d) S. Yang, B. Li, X. Wan, Z. Shi, J. Am. Chem. Soc. 2007, 129, 6066-6067;
  • 64
    • 21244438753 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2005, 44, 4046-4048;
    • (2005) Angew. Chem. Int. Ed , vol.44 , pp. 4046-4048
  • 67
    • 30744445455 scopus 로고    scopus 로고
    • oxazoles: j X. Chen, J.-J. Li, X.-S. Hao, C. E. Goodhue, Ji.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 78-79;
    • oxazoles: j) X. Chen, J.-J. Li, X.-S. Hao, C. E. Goodhue, Ji.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 78-79;
  • 70
    • 54849420705 scopus 로고    scopus 로고
    • carboxylic acids: m R. Giri, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 14082-14083;
    • carboxylic acids: m) R. Giri, J.-Q. Yu, J. Am. Chem. Soc. 2008, 130, 14082-14083;
  • 72
    • 0028139171 scopus 로고    scopus 로고
    • For E/Z isomerization of vinylpalladium species, see, for example: a G. Dyker, A. Kellner, Tetrahedron Lett. 1994, 35, 7633-7636;
    • For E/Z isomerization of vinylpalladium species, see, for example: a) G. Dyker, A. Kellner, Tetrahedron Lett. 1994, 35, 7633-7636;
  • 75
    • 66149094435 scopus 로고    scopus 로고
    • See also ref.[1
    • [1]
  • 76
    • 0001642264 scopus 로고    scopus 로고
    • See Supporting Information
    • Q. Tian, R. C. Larock, Org. Lett. 2000, 2, 3329. See Supporting Information.
    • (2000) Org. Lett , vol.2 , pp. 3329
    • Tian, Q.1    Larock, R.C.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.