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Volumn 11, Issue 11, 2009, Pages 2325-2328

Electron-poor chiral diphosphine ligands: High performance for rh-catalyzed asymmetric 1,4-addition of arylboronic acids at room temperature

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[No Author keywords available]

Indexed keywords


EID: 66149162965     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900719z     Document Type: Article
Times cited : (75)

References (53)
  • 22
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    • Among them, Difluorphos (ref 5b) has been used recently. Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195.
    • Among them, Difluorphos (ref 5b) has been used recently. Liao, X.; Weng, Z.; Hartwig, J. F. J. Am. Chem. Soc. 2008, 130, 195.
  • 28
    • 66149171401 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr. Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S; Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keith
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A.; Jr. Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision E.01; Gaussian, Inc.: Pittsburgh, PA, 2004.
  • 34
    • 17244368456 scopus 로고    scopus 로고
    • The low catalytic activity of the Rh-1a catalyst can perhaps be attributed to a steric effect of the 2,6-position of the fluorine atom in the Ar group: Clarke, M. L.; Ellis, D.; Mason, K. L.; Orpen, A. G.; Pringle, P. G.; Wingad, R. L.; Zaher, D. A.; Baker, R. T. Dalton Trans. 2005, 7, 1294.
    • The low catalytic activity of the Rh-1a catalyst can perhaps be attributed to a steric effect of the 2,6-position of the fluorine atom in the Ar group: Clarke, M. L.; Ellis, D.; Mason, K. L.; Orpen, A. G.; Pringle, P. G.; Wingad, R. L.; Zaher, D. A.; Baker, R. T. Dalton Trans. 2005, 7, 1294.
  • 35
    • 43249097055 scopus 로고    scopus 로고
    • The result that the electron-poor ligand is superior to BINAP is consistent with those of Rh-catalyzed 1,4-addition to other R, unsaturated substrates by using Difluorophos. Navarre, L, Martinez, R, Genet, J.-P, Darses, S. J. Am. Chem. Soc. 2008, 130, 6159
    • The result that the electron-poor ligand is superior to BINAP is consistent with those of Rh-catalyzed 1,4-addition to other R,-- unsaturated substrates by using Difluorophos. Navarre, L.; Martinez, R.; Genet, J.-P.; Darses, S. J. Am. Chem. Soc. 2008, 130, 6159.
  • 37
    • 31444457133 scopus 로고    scopus 로고
    • Hayashi et al. reported that the reaction using 0.05 mol % of the Rh catalyst and 1.2 equiv of 7a at 30 °C for 1 h gave 95% of product with 96% ee (TOF ) 1900 h-1) and the use of (PhBO)3 instead of 7a gave a TOF value of 14000 h-1. Minnaard and Feringa et al. reported that the reaction using 0.05 mol % of the Rh catalyst and 3 equiv of 7a at 80 °C for 2 h gave 100% of product with >98% ee (TOF ) 1000 h-1). Chen, F.-X.; Kina, A.; Hayashi, T. Org. Lett. 2006, 8, 341.
    • Hayashi et al. reported that the reaction using 0.05 mol % of the Rh catalyst and 1.2 equiv of 7a at 30 °C for 1 h gave 95% of product with 96% ee (TOF ) 1900 h-1) and the use of (PhBO)3 instead of 7a gave a TOF value of 14000 h-1. Minnaard and Feringa et al. reported that the reaction using 0.05 mol % of the Rh catalyst and 3 equiv of 7a at 80 °C for 2 h gave 100% of product with >98% ee (TOF ) 1000 h-1). Chen, F.-X.; Kina, A.; Hayashi, T. Org. Lett. 2006, 8, 341.
  • 39
    • 66149160290 scopus 로고    scopus 로고
    • Except for the prominent results in ref 17, the TOF values of most catalytic systems are less than 100 in Rh-catalyzed asymmetric 1,4-addion of PhB(OH)2 to 1,2-cyclohexenone.
    • Except for the prominent results in ref 17, the TOF values of most catalytic systems are less than 100 in Rh-catalyzed asymmetric 1,4-addion of PhB(OH)2 to 1,2-cyclohexenone.
  • 40
    • 60849111703 scopus 로고    scopus 로고
    • The same reaction as shown in Table 2 at room temperature (20-25 °C). Lukin, K.; Zhang, Q.; Leanna, M. R. J. Org. Chem. 2009, 74, 929.
    • The same reaction as shown in Table 2 at room temperature (20-25 °C). Lukin, K.; Zhang, Q.; Leanna, M. R. J. Org. Chem. 2009, 74, 929.
  • 52
    • 66149190603 scopus 로고    scopus 로고
    • The [RhCl
    • The [RhCl
  • 53
    • 0038034717 scopus 로고    scopus 로고
    • complex without KOH showed no catalytic activity at low temperature. Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000.
    • complex without KOH showed no catalytic activity at low temperature. Itooka, R.; Iguchi, Y.; Miyaura, N. J. Org. Chem. 2003, 68, 6000.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.