메뉴 건너뛰기




Volumn 11, Issue 10, 2009, Pages 2045-2048

Copper(0)-induced deselenative insertion of N,N-disubstituted selenoamides into acetylenic C-H bond leading to propargylamines

Author keywords

[No Author keywords available]

Indexed keywords


EID: 66149131036     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9001976     Document Type: Article
Times cited : (30)

References (138)
  • 1
    • 57549119091 scopus 로고    scopus 로고
    • For recent reviews, see, for example: a
    • For recent reviews, see, for example: (a) Würtz, S.; Glorius, F. Acc. Chem. Res. 2008, 41, 1523.
    • (2008) Acc. Chem. Res , vol.41 , pp. 1523
    • Würtz, S.1    Glorius, F.2
  • 22
    • 0034246704 scopus 로고    scopus 로고
    • Yet, L. Chem. Rev. 2000, 100, 2963.
    • (2000) Chem. Rev , vol.100 , pp. 2963
    • Yet, L.1
  • 24
    • 66149084521 scopus 로고    scopus 로고
    • Metal Carbenes in Organic Synthesis. In Topics in Organometallic Chemistry; Dötz, K. H., Ed.; Springer: Berlin, 2004; 13.
    • Metal Carbenes in Organic Synthesis. In Topics in Organometallic Chemistry; Dötz, K. H., Ed.; Springer: Berlin, 2004; Vol. 13.
  • 25
    • 34547338866 scopus 로고    scopus 로고
    • N-Heterocyclic Carbenes in Transition Metal Catalysis
    • Glorius, F, Ed, Springer: Berlin
    • N-Heterocyclic Carbenes in Transition Metal Catalysis. In Topics in Organometallic Chemistry; Glorius, F., Ed.; Springer: Berlin, 2007; Vol. 21.
    • (2007) Topics in Organometallic Chemistry , vol.21
  • 26
    • 51249111083 scopus 로고    scopus 로고
    • For the transition-metal-catalyzed reaction of Fischer-carbene complexes, which C=M (M = Cr and W) bonds were activated by transition-metal complexes in mild conditions. For these reactions, see: (a) Meana, I.; Albéniz, A. C.; Espinet, P. Organometallics 2008, 27, 4193.
    • For the transition-metal-catalyzed reaction of Fischer-carbene complexes, which C=M (M = Cr and W) bonds were activated by transition-metal complexes in mild conditions. For these reactions, see: (a) Meana, I.; Albéniz, A. C.; Espinet, P. Organometallics 2008, 27, 4193.
  • 48
    • 0001729405 scopus 로고
    • Trost, B. M, Ed, Pergamon: New York, Chapter 2.6, p
    • Ogawa, A.; Sonoda, N. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon: New York, 1991; Vol. 6, Chapter 2.6, p 461.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 461
    • Ogawa, A.1    Sonoda, N.2
  • 49
    • 0001600151 scopus 로고    scopus 로고
    • Wirth, T, Ed, Springer: Berlin
    • Murai, T.; Kato, S. In Top. Curr. Chem.; Wirth, T., Ed.; Springer: Berlin, 2000; Vol. 208, p 177.
    • (2000) Top. Curr. Chem , vol.208 , pp. 177
    • Murai, T.1    Kato, S.2
  • 75
    • 11844290670 scopus 로고    scopus 로고
    • For the synthesis of propargylamines using organolithium reagents, see, for example: a
    • For the synthesis of propargylamines using organolithium reagents, see, for example: (a) Katritzky, A. R.; Yang, H.; Singh, S. K. J. Org. Chem. 2005, 70, 286.
    • (2005) J. Org. Chem , vol.70 , pp. 286
    • Katritzky, A.R.1    Yang, H.2    Singh, S.K.3
  • 80
    • 34548426047 scopus 로고    scopus 로고
    • For the synthesis of propargylamines using organozinc reagents, see, for example: a
    • For the synthesis of propargylamines using organozinc reagents, see, for example: (a) Ramu, E.; Varala, R.; Sreelatha, N.; Adapa, S. R. Tetrahedron Lett. 2007, 48, 7184.
    • (2007) Tetrahedron Lett , vol.48 , pp. 7184
    • Ramu, E.1    Varala, R.2    Sreelatha, N.3    Adapa, S.R.4
  • 86
    • 33745697773 scopus 로고    scopus 로고
    • For the synthesis of propargylamines using organocopper reagents, see, for example: a
    • For the synthesis of propargylamines using organocopper reagents, see, for example: (a) Bisai, A.; Singh, V. K. Org. Lett. 2006, 8, 2405.
    • (2006) Org. Lett , vol.8 , pp. 2405
    • Bisai, A.1    Singh, V.K.2
  • 96
    • 35348851365 scopus 로고    scopus 로고
    • For the synthesis of propargylamines using other organometallic reagents, see, for example: a
    • For the synthesis of propargylamines using other organometallic reagents, see, for example: (a) Turcaud, S.; Berhal, F.; Royer, J. J. Org. Chem. 2007, 72, 7893.
    • (2007) J. Org. Chem , vol.72 , pp. 7893
    • Turcaud, S.1    Berhal, F.2    Royer, J.3
  • 120
    • 58649118017 scopus 로고    scopus 로고
    • For the recent review for the propargylamines, see, for example: a
    • For the recent review for the propargylamines, see, for example: (a) Kouznetsov, V. V.; Vargas Méndez, L. Y. Synthesis 2008, 491.
    • (2008) Synthesis , pp. 491
    • Kouznetsov, V.V.1    Vargas Méndez, L.Y.2
  • 123
    • 33845205545 scopus 로고    scopus 로고
    • For the spectral and analytical data of 1,3,5-triethyl benzene-1,3,5-tricarboxylate and 1,2,4-triethyl benzene-1,2,4-tricarboxylate, see: a
    • For the spectral and analytical data of 1,3,5-triethyl benzene-1,3,5-tricarboxylate and 1,2,4-triethyl benzene-1,2,4-tricarboxylate, see: (a) Cadi-erno, V.; García-Garrido, S. E.; Gimeno, J. J. Am. Chem. Soc. 2006, 128, 15094.
    • (2006) J. Am. Chem. Soc , vol.128 , pp. 15094
    • Cadi-erno, V.1    García-Garrido, S.E.2    Gimeno, J.3
  • 125
    • 66149102527 scopus 로고    scopus 로고
    • In the cases of other acetylenes, trace amounts of enyne, diyne, and cyclotrimerization products were obtained. These results indicated that the Cu(I) or Cu(II) species was generated from copper powder in this reaction system, and these copper species afforded dimerization or cyclotrimerization products of acetylene
    • In the cases of other acetylenes, trace amounts of enyne, diyne, and cyclotrimerization products were obtained. These results indicated that the Cu(I) or Cu(II) species was generated from copper powder in this reaction system, and these copper species afforded dimerization or cyclotrimerization products of acetylene.
  • 126
    • 53849097713 scopus 로고    scopus 로고
    • For the copper-catalyzed dimerization reaction of terminal acetylenes to give the corresponding diynes, see: (a) Alcaide, B, Almendros, P, Carrascosa, R, Rodríguez-Acebes, R, Chem. 2008, 1575
    • For the copper-catalyzed dimerization reaction of terminal acetylenes to give the corresponding diynes, see: (a) Alcaide, B.; Almendros, P.; Carrascosa, R.; Rodríguez-Acebes, R. Eur. J. Org. Chem. 2008, 1575.
  • 132
    • 0006933444 scopus 로고
    • The copper-catalyzed cyclotrimerization reaction of unsaturated bonds, see
    • Ficini, J.; d'Angelo, J.; Falou, S. Tetrahedron Lett. 1977, 18, 1645. The copper-catalyzed cyclotrimerization reaction of unsaturated bonds, see:
    • (1977) Tetrahedron Lett , vol.18 , pp. 1645
    • Ficini, J.1    d'Angelo, J.2    Falou, S.3
  • 136
    • 26444457273 scopus 로고    scopus 로고
    • The 1H and 13C NMR spectra and chemical shift of 4a were shown in this paper, see: Reddy, C, Reddy, V, Urgaonkar, S, Verkade, J. G. Org. Lett. 2005, 7, 4427
    • 13C NMR spectra and chemical shift of 4a were shown in this paper, see: Reddy, C.; Reddy, V.; Urgaonkar, S.; Verkade, J. G. Org. Lett. 2005, 7, 4427.
  • 137
    • 46649088926 scopus 로고    scopus 로고
    • The copper(I)-mediated H/D exchange reaction of terminal acetylene was reported, see: (a) Tachiyama, T.; Yoshida, M.; Aoyagi, T.; Fukuzumi, S. J. Phys. Org. Chem. 2008, 21, 510.
    • The copper(I)-mediated H/D exchange reaction of terminal acetylene was reported, see: (a) Tachiyama, T.; Yoshida, M.; Aoyagi, T.; Fukuzumi, S. J. Phys. Org. Chem. 2008, 21, 510.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.