메뉴 건너뛰기




Volumn 10, Issue 16, 2008, Pages 3409-3412

Ruthenium-catalyzed hydroarylations of methylenecyclopropanes: Mild C-H bond functionalizations with conservation of cyclopropane rings

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANE DERIVATIVE; LIGAND; METHYLENECYCLOPROPANE; ORGANOMETALLIC COMPOUND; RUTHENIUM;

EID: 54049085812     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8011875     Document Type: Article
Times cited : (92)

References (65)
  • 1
    • 35248816863 scopus 로고    scopus 로고
    • Recent reviews on C-H bond functionalizations, see: a
    • Recent reviews on C-H bond functionalizations, see: (a) Ackermann, L. Top. Organomet. Chem 2007, 24, 35-60.
    • (2007) Top. Organomet. Chem , vol.24 , pp. 35-60
    • Ackermann, L.1
  • 10
    • 33744510833 scopus 로고    scopus 로고
    • Dyker, G, Ed, Wiley-VCH: Weinheim
    • (a) Dyker, G., Ed. Handbook of C-H Transformations; Wiley-VCH: Weinheim, 2005.
    • (2005) Handbook of C-H Transformations
  • 16
    • 41449111035 scopus 로고    scopus 로고
    • Selected related intermolecular hydroarylations catalyzed by metals other than ruthenium: (a) Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645-3651.
    • Selected related intermolecular hydroarylations catalyzed by metals other than ruthenium: (a) Colby, D. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 3645-3651.
  • 28
    • 17844369291 scopus 로고    scopus 로고
    • Murahashi, S.-L, Ed, Wiley-VCH: Weinheim, and references cited therein
    • (c) Kakiuchi, F.; Chatani, N. In Ruthenium in Organic Synthesis; Murahashi, S.-L, Ed.; Wiley-VCH: Weinheim, 2004; pp 219-255, and references cited therein.
    • (2004) Ruthenium in Organic Synthesis , pp. 219-255
    • Kakiuchi, F.1    Chatani, N.2
  • 29
    • 34249819055 scopus 로고    scopus 로고
    • Selected additional ruthenium-catalyzed hydroarylations: (a) Foley, N. A.; Lail, M.; Lee, J. P.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. J. Am. Chem. Soc. 2007, 129, 6765-6781.
    • Selected additional ruthenium-catalyzed hydroarylations: (a) Foley, N. A.; Lail, M.; Lee, J. P.; Gunnoe, T. B.; Cundari, T. R.; Petersen, J. L. J. Am. Chem. Soc. 2007, 129, 6765-6781.
  • 33
    • 0000463307 scopus 로고
    • and references cited therein
    • (e) Lewis, L. N.; Smith, J. F. J. Am. Chem. Soc. 1986, 108, 2728-2735, and references cited therein.
    • (1986) J. Am. Chem. Soc , vol.108 , pp. 2728-2735
    • Lewis, L.N.1    Smith, J.F.2
  • 36
    • 61349177361 scopus 로고    scopus 로고
    • Reviews on metal-promoted reactions of methylenecyclopropanes: (a) Binger, P.; Schmidt, T. In Houben-Weyl; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; E17c, pp 2217-2294.
    • Reviews on metal-promoted reactions of methylenecyclopropanes: (a) Binger, P.; Schmidt, T. In Houben-Weyl; de Meijere, A., Ed.; Thieme: Stuttgart, 1997; Vol. E17c, pp 2217-2294.
  • 39
    • 4444374674 scopus 로고    scopus 로고
    • Only a few catalytic reactions were thus far reported, not resulting in an opening of at least one cyclopropane ring: (a) Takeuchi, D.; Anada, K.; Osakada, K. Angew. Chem., Int. Ed. 2004, 43, 1233-1235.
    • Only a few catalytic reactions were thus far reported, not resulting in an opening of at least one cyclopropane ring: (a) Takeuchi, D.; Anada, K.; Osakada, K. Angew. Chem., Int. Ed. 2004, 43, 1233-1235.
  • 43
    • 36849005573 scopus 로고    scopus 로고
    • A recent elegant intramolecular rhodium-catalyzed C-H bond activation with alkylidenecyclopropanes also resulted in ring opening of the cyclopropane moiety; Aïssa, C, Fürstner, A. J. Am. Chem. Soc. 2007, 129, 14836-14837
    • A recent elegant intramolecular rhodium-catalyzed C-H bond activation with alkylidenecyclopropanes also resulted in ring opening of the cyclopropane moiety; Aïssa, C.; Fürstner, A. J. Am. Chem. Soc. 2007, 129, 14836-14837.
  • 44
    • 61349110475 scopus 로고    scopus 로고
    • Selected reports from our laboratories on ruthenium-catalyzed C-H bond functionalizations: (a) Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2008, 2299-2302.
    • Selected reports from our laboratories on ruthenium-catalyzed C-H bond functionalizations: (a) Ackermann, L.; Vicente, R.; Althammer, A. Org. Lett. 2008, 2299-2302.
  • 48
  • 49
    • 61349172887 scopus 로고    scopus 로고
    • 2 and PPhs yielded quantitative ring opening of 2, along with its polymerization, even at 50 °C reaction temperature.
    • 2 and PPhs yielded quantitative ring opening of 2, along with its polymerization, even at 50 °C reaction temperature.
  • 50
    • 61349186745 scopus 로고    scopus 로고
    • Here, only undesired by-products due to Diels-Alder [4 + 2] cycloadditions of 2-phenylbuta-l,4-diene were obtained (see the Supporting Information).
    • Here, only undesired by-products due to Diels-Alder [4 + 2] cycloadditions of 2-phenylbuta-l,4-diene were obtained (see the Supporting Information).
  • 53
    • 61349193564 scopus 로고    scopus 로고
    • CCDC-678126 (b), -688765 (13b), and -678125 (14) contain the supplementary crystallographic data for these compounds. The data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam. ac-uk.
    • CCDC-678126 (b), -688765 (13b), and -678125 (14) contain the supplementary crystallographic data for these compounds. The data can be obtained free of charge via www.ccdc.cam.ac.uk/conts/retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam. ac-uk.
  • 54
    • 0035540115 scopus 로고    scopus 로고
    • A deuterium-proton exchange was previously observed in hydroarylations of simple alkenes: (a) Kakiuchi, F.; Ohtaki, H.; Sonoda, M.; Chatani, N.; Murai, S. Chem. Lett. 2001, 30, 918-919.
    • A deuterium-proton exchange was previously observed in hydroarylations of simple alkenes: (a) Kakiuchi, F.; Ohtaki, H.; Sonoda, M.; Chatani, N.; Murai, S. Chem. Lett. 2001, 30, 918-919.
  • 56
    • 61349105715 scopus 로고    scopus 로고
    • 7] as solvent, proton-deuterium exchange on pyridines 1a and 3a was not observed under otherwise identical reaction conditions.
    • 7] as solvent, proton-deuterium exchange on pyridines 1a and 3a was not observed under otherwise identical reaction conditions.
  • 57
    • 38149032348 scopus 로고    scopus 로고
    • The high selectivity obtained with monophosphine biphenyl ligand 11 is likely due to formation of arene-tethered ruthenium phosphine complexes. For the use of comparable phosphines in ruthenium catalysis, see: (a) Aikawa, K.; Kaito, I.; Mikami, K. Chem. Lett. 2007, 36, 1482-1483.
    • The high selectivity obtained with monophosphine biphenyl ligand 11 is likely due to formation of arene-tethered ruthenium phosphine complexes. For the use of comparable phosphines in ruthenium catalysis, see: (a) Aikawa, K.; Kaito, I.; Mikami, K. Chem. Lett. 2007, 36, 1482-1483.
  • 58
    • 34047273944 scopus 로고    scopus 로고
    • and references cited therein
    • (b) Faller, J. W.; Fontaine, P. P. Organometallics 2007, 26, 1738-1743, and references cited therein.
    • (2007) Organometallics , vol.26 , pp. 1738-1743
    • Faller, J.W.1    Fontaine, P.P.2
  • 59
    • 61349152749 scopus 로고    scopus 로고
    • The corresponding arene-tethered ruthenium phosphine complex derived from ligand 11 was isolated and unambigiously characterized: Kozhushkov, S. I.; Yufit, D. S.; Ackermann, L. Unpublished results.
    • The corresponding arene-tethered ruthenium phosphine complex derived from ligand 11 was isolated and unambigiously characterized: Kozhushkov, S. I.; Yufit, D. S.; Ackermann, L. Unpublished results.
  • 60
    • 2742566089 scopus 로고
    • Thieme: Stuttgart
    • (a) Wendisch, D. In Houben-Weyl; Thieme: Stuttgart, 1971; Vol. 4/3, pp 399-405.
    • (1971) Houben-Weyl , vol.4 , Issue.3 , pp. 399-405
    • Wendisch, D.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.