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Volumn 74, Issue 24, 2009, Pages 9351-9358

Generation of allenic/propargylic zirconium complexes and subsequent cross-coupling reactions: A facile synthesis of multisubstituted allenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKOXIDES; ALLENES; ARYL IODIDES; CHEMICAL EQUATIONS; COUPLING REACTION; CROSS COUPLING REACTIONS; DFT CALCULATION; ELIMINATION REACTION; FACILE SYNTHESIS; PRODUCT DISTRIBUTIONS; STERIC EFFECT; SUBSTITUTION PATTERNS; ZIRCONIUM COMPLEXES;

EID: 73149112197     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9020419     Document Type: Article
Times cited : (24)

References (73)
  • 40
    • 0001668584 scopus 로고
    • Selected papers for the synthesis of allenes, see: a
    • Selected papers for the synthesis of allenes, see: (a) Rona, P.; Crabbé, P. J. Am. Chem. Soc. 1969, 91, 3289.
    • (1969) J. Am. Chem. Soc , vol.91 , pp. 3289
    • Rona, P.1    Crabbé, P.2
  • 50
    • 33645897044 scopus 로고    scopus 로고
    • For palladium-catalyzed coupling reactions of propargylic esters, mesylates, or carbonates with Grignard or zinc reagents, etc, see: k
    • For palladium-catalyzed coupling reactions of propargylic esters, mesylates, or carbonates with Grignard or zinc reagents, etc., see: (k) Riveiros, R.; Rodríguez, D.; Sestelo, J. P.; Sarandeses, L. A. Org. Lett. 2006, 8, 1403.
    • (2006) Org. Lett , vol.8 , pp. 1403
    • Riveiros, R.1    Rodríguez, D.2    Sestelo, J.P.3    Sarandeses, L.A.4
  • 57
    • 73149118120 scopus 로고    scopus 로고
    • NMR data of allenic zirconium species derived from (3-methoxy-4- methylpent-1-ynyl)benzene 1h has been reported; see ref 3b
    • NMR data of allenic zirconium species derived from (3-methoxy-4- methylpent-1-ynyl)benzene 1h has been reported; see ref 3b.
  • 58
    • 73149123659 scopus 로고    scopus 로고
    • See the Supporting Information
    • See the Supporting Information.
  • 61
    • 73149120594 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, Frisch, M. J, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, 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, Dannengerg, 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, K
    • 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.; Frisch, M. J.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; 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.; Dannengerg, 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 C.02; Gaussian, Inc.: Wallingford, CT, 2004.
  • 65
    • 73149118782 scopus 로고    scopus 로고
    • For the reaction of propargyl ether without substituent at the C-1 carbon such as (3-(benzyloxy)prop-1-ynyl)benzene with 2 equiv of Negishi reagent, see ref 3b. The reaction produced (Z)-β-methylstyrene as a sole product, which was explained by addition of Cp2Zr to propargyl zirconium species
    • 2Zr" to propargyl zirconium species.
  • 67
    • 73149100204 scopus 로고    scopus 로고
    • The experimental NMR shift of C6 might be overlapped with Cp impurities in the range of 110.3-114.1 ppm.
    • The experimental NMR shift of C6 might be overlapped with Cp impurities in the range of 110.3-114.1 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.