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Volumn 129, Issue 32, 2007, Pages 9858-9859

The Ru(cod)(cot)-catalyzed alkenylation of aromatic C-H bonds with alkenyl acetates

Author keywords

[No Author keywords available]

Indexed keywords

1,3,5 CYCLOOCTATRIENE; 1,5 CYCLOOCTADIENE; ACETIC ACID DERIVATIVE; ALKADIENE; ALKENE; AROMATIC COMPOUND; CARBON; HYDROGEN; RUTHENIUM; UNCLASSIFIED DRUG;

EID: 34547911383     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja071965m     Document Type: Article
Times cited : (141)

References (34)
  • 3
    • 17844365805 scopus 로고    scopus 로고
    • Bruneau, C, Dixneuf, P. H, Eds, Springer-Verlag: Berlin
    • (c) Kakiuchi, F.; Chatani, N. In Topics in Organometallic Chemistry; Bruneau, C., Dixneuf, P. H., Eds.; Springer-Verlag: Berlin, 2004; Vol. 11, pp 45-79.
    • (2004) Topics in Organometallic Chemistry , vol.11 , pp. 45-79
    • Kakiuchi, F.1    Chatani, N.2
  • 27
    • 33846918696 scopus 로고    scopus 로고
    • Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238. See also refs 1 and 2b.
    • (e) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174-238. See also refs 1 and 2b.
  • 29
    • 34547878116 scopus 로고    scopus 로고
    • Several other transition metal complexes such as Ru3(CO) 12, RhCl(coe)2]2, RhCl(coe)2] 2/PCy3, RuH2(CO)(PPh3)3, Ru(CO)3(PPh3)2, RuHCl(CO)(PPh3) 3, RuH(OAc)(CO)(PPh3)2, RuCl 2(C6H6)]2/PPh3, RhCl(PPh3)3, and Pd(OAc)2/PPh3 were also screened, but no improvement of the yields was observed 0-21% yields
    • 3 were also screened, but no improvement of the yields was observed (0-21% yields).
  • 30
    • 34547911176 scopus 로고    scopus 로고
    • After the discovery of the reaction conditions for Table 1, entry 6, we examined vinylation of 1 with alkenyl acetates in the presence of trifurylphosphine. However, these attempts only resulted in lower yields.
    • After the discovery of the reaction conditions for Table 1, entry 6, we examined vinylation of 1 with alkenyl acetates in the presence of trifurylphosphine. However, these attempts only resulted in lower yields.
  • 31
    • 0035323796 scopus 로고    scopus 로고
    • The reason for the beneficial effect of 17 remains elusive at present, but the use of 17 has frequently been reported to be advantageous in transition metal-mediated organic reactions; Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997-1030.
    • The reason for the beneficial effect of 17 remains elusive at present, but the use of 17 has frequently been reported to be advantageous in transition metal-mediated organic reactions; Andersen, N. G.; Keay, B. A. Chem. Rev. 2001, 101, 997-1030.
  • 32
    • 12144291658 scopus 로고    scopus 로고
    • 1H NMR spectrum was similar to those of some reported ortho-ruthenated phenylpyridine complexes; Matthes, J.; Grundemann, S.; Toner, A.; Guari, Y.; Donnadieu, B.; Spandl, J.; Sabo-Etienne, S.; Clot, E.; Limbach, H.-H.; Chaudret, B. Organometallics 2004, 23, 1424-1433.
    • 1H NMR spectrum was similar to those of some reported ortho-ruthenated phenylpyridine complexes; Matthes, J.; Grundemann, S.; Toner, A.; Guari, Y.; Donnadieu, B.; Spandl, J.; Sabo-Etienne, S.; Clot, E.; Limbach, H.-H.; Chaudret, B. Organometallics 2004, 23, 1424-1433.
  • 33
    • 34547923855 scopus 로고    scopus 로고
    • See Supporting Information for further details on mechanistic studies
    • See Supporting Information for further details on mechanistic studies.
  • 34
    • 33749844953 scopus 로고    scopus 로고
    • Very recently, Oi et al. reported that the [RuCl2cod, n/PPh3-catalyzed reaction of arylpyridines with allyl acetates gave a mixture of ortho allylation and alkenylation products. We believe the mechanism of this reaction is different from our reaction described here due to much lower catalytic activity of our reaction under Oi's reaction conditions. See Supporting Information for further details: Oi, S, Tanaka, Y, Inoue, Y. Organometallics 2006, 25, 4773-4778
    • 3-catalyzed reaction of arylpyridines with allyl acetates gave a mixture of ortho allylation and alkenylation products. We believe the mechanism of this reaction is different from our reaction described here due to much lower catalytic activity of our reaction under Oi's reaction conditions. See Supporting Information for further details: Oi, S.; Tanaka, Y.; Inoue, Y. Organometallics 2006, 25, 4773-4778.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.