메뉴 건너뛰기




Volumn 133, Issue 12, 2011, Pages 4330-4341

Pd-catalyzed carbonylation of diazo compounds at atmospheric pressure: A catalytic approach to ketenes

Author keywords

[No Author keywords available]

Indexed keywords

[2 + 2] CYCLOADDITION; [4 + 2] CYCLOADDITION; ACYLKETENES; CARBENES; CATALYTIC CYCLES; DFT CALCULATION; DIASTEREO-SELECTIVITY; DIAZO COMPOUNDS; DIAZOKETONES; GOOD YIELD; IN-SITU; MEDIATED REACTIONS; NEW APPROACHES; ORGANIC SYNTHESIS; PALLADIUM CATALYST; REACTION MECHANISM;

EID: 79953033547     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja107351d     Document Type: Article
Times cited : (169)

References (150)
  • 7
    • 0031585112 scopus 로고    scopus 로고
    • For carbonylation of Fischer carbene complexes, see
    • For carbonylation of Fischer carbene complexes, see: Hegedus, L. S. Tetrahedron 1997, 53, 4105
    • (1997) Tetrahedron , vol.53 , pp. 4105
    • Hegedus, L.S.1
  • 55
    • 22944454156 scopus 로고    scopus 로고
    • For the most recent reviews, see
    • For the most recent reviews, see: Cacchi, S.; Fabrizi, G. Chem. Rev. 2005, 105, 2873
    • (2005) Chem. Rev. , vol.105 , pp. 2873
    • Cacchi, S.1    Fabrizi, G.2
  • 75
    • 0035844718 scopus 로고    scopus 로고
    • For catalytic reactions involving Pd carbene species, see
    • For catalytic reactions involving Pd carbene species, see: Greenman, K. L.; Carter, D. S.; Van Vranken, D. L. Tetrahedron 2001, 57, 5219
    • (2001) Tetrahedron , vol.57 , pp. 5219
    • Greenman, K.L.1    Carter, D.S.2    Van Vranken, D.L.3
  • 90
    • 0000709206 scopus 로고
    • For selected reviews on diazo compounds, see
    • For selected reviews on diazo compounds, see: Ye, T.; McKervey, M. A. Chem. Rev. 1994, 94, 1091
    • (1994) Chem. Rev. , vol.94 , pp. 1091
    • Ye, T.1    McKervey, M.A.2
  • 94
    • 70350494959 scopus 로고    scopus 로고
    • For a recent review on acylketenes, see:;, For selected reports, see:; Chem. Pharm. Bull. 1984, 32, 2602
    • For a recent review on acylketenes, see: Reber, K. P.; Tilley, S. D.; Sorensen, E. J. Chem. Soc. Rev. 2009, 38, 3022 For selected reports, see: Sato, M.; Ogasawara, H.; Tato, T. Chem. Pharm. Bull. 1984, 32, 2602
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 3022
    • Reber, K.P.1    Tilley, S.D.2    Sorensen, E.J.3    Sato, M.4    Ogasawara, H.5    Tato, T.6
  • 104
    • 79953057749 scopus 로고    scopus 로고
    • For details, see Table S1 in the Supporting Information.
    • For details, see Table S1 in the Supporting Information.
  • 124
    • 79953035814 scopus 로고    scopus 로고
    • See Supporting Information for details.
    • See Supporting Information for details.
  • 139
    • 49349108183 scopus 로고    scopus 로고
    • Interestingly, a reverse process, namely the formation of Pd carbene from ketene has been recently reported, see
    • Interestingly, a reverse process, namely the formation of Pd carbene from ketene has been recently reported, see: Goll, J. M.; Fillion, E. Organometallics 2008, 27, 3622
    • (2008) Organometallics , vol.27 , pp. 3622
    • Goll, J.M.1    Fillion, E.2
  • 140
    • 33845470390 scopus 로고
    • For torquoelectronics effect of cyclobutenes, see
    • For torquoelectronics effect of cyclobutenes, see: Kirmse, W.; Rondan, N. G.; Houk, K. N. J. Am. Chem. Soc. 1984, 106, 7989
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 7989
    • Kirmse, W.1    Rondan, N.G.2    Houk, K.N.3
  • 146
    • 33751385142 scopus 로고
    • For torquoelectronics effect of Staudinger reaction, see
    • For torquoelectronics effect of Staudinger reaction, see: López, R.; Sordo, T. L.; Sordo, J. A.; González, J. J. Org. Chem. 1993, 58, 7036
    • (1993) J. Org. Chem. , vol.58 , pp. 7036
    • López, R.1    Sordo, T.L.2    Sordo, J.A.3    González, J.4
  • 149
    • 79953034228 scopus 로고    scopus 로고
    • note
    • In the reaction of photogenerated metallaketenes and imines, the participation of the metal moiety in the [2 + 2] cycloaddition has been evidenced by the use of chiral chromium(0) alkoxycarbene complex, which affords β-lactam with low but significant ee. See ref 20m.
  • 150
    • 0037049168 scopus 로고    scopus 로고
    • For an example of Pd-catalyzed carbonylation of diazonium salts, see
    • For an example of Pd-catalyzed carbonylation of diazonium salts, see: Andrus, M. B.; Ma, Y.; Zang, Y.; Song, C. Tetrahedron Lett. 2002, 43, 9137
    • (2002) Tetrahedron Lett. , vol.43 , pp. 9137
    • Andrus, M.B.1    Ma, Y.2    Zang, Y.3    Song, C.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.