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Volumn 70, Issue 21, 2005, Pages 8638-8641

Palladium-catalyzed synthesis of N-vinyl pyrroles and indoles

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; DERIVATIVES; PALLADIUM; SUBSTRATES; SYNTHESIS (CHEMICAL);

EID: 26844546901     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051450i     Document Type: Article
Times cited : (58)

References (67)
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    • For a recent review on the use of copper in cross-coupling reactions, see: (a) Beletskaya, I. P.; Cheprakov, A. V. Coord. Chem. Rev. 2004, 248, 2337-2364.
    • (2004) Coord. Chem. Rev. , vol.248 , pp. 2337-2364
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  • 33
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    • (h) Hu, T.; Li, C. Org. Lett. 2005, 7, 2035-2038.
    • (2005) Org. Lett. , vol.7 , pp. 2035-2038
    • Hu, T.1    Li, C.2
  • 36
    • 20444449293 scopus 로고    scopus 로고
    • For a copper-catalyzed C-N bond formation using allenyl halides, see: (k) Trost, B. M.; Stiles, D. T. Org. Lett. 2005, 7, 2117-2120.
    • (2005) Org. Lett. , vol.7 , pp. 2117-2120
    • Trost, B.M.1    Stiles, D.T.2
  • 47
    • 0027180141 scopus 로고
    • For reviews on the preparation and use of vinyl triflates, see: (a) Ritter, K. Synthesis 1993, 735-762.
    • (1993) Synthesis , pp. 735-762
    • Ritter, K.1
  • 50
    • 26844517620 scopus 로고    scopus 로고
    • note
    • Use of XPhos gave superior results as compared to tri-(o-tolyl)- phosphine, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), and 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (SPhos).
  • 52
    • 26844543037 scopus 로고    scopus 로고
    • note
    • (b) XPhos is commercially available.
  • 53
    • 26844538263 scopus 로고    scopus 로고
    • note
    • In the absence of palladium catalyst, none of the coupling products were observed.
  • 54
    • 26844554657 scopus 로고    scopus 로고
    • note
    • Best results were obtained by further drying commercially available anhydrous potassium phosphate (160 °C, 0.1 Torr, 12 h) and handling it under inert atmosphere.
  • 55
    • 0031021265 scopus 로고    scopus 로고
    • For a discussion on the competitive elimination reaction to give ynoates in studies concerning the palladium-catalyzed C-O and C-S bond formation, see: Rossi, R.; Bellina, F.; Mannina, L. Tetrahedron 1997, 53, 1025-1044.
    • (1997) Tetrahedron , vol.53 , pp. 1025-1044
    • Rossi, R.1    Bellina, F.2    Mannina, L.3
  • 56
    • 0000436963 scopus 로고
    • For the synthesis of AT-(tributylstannyl)pyrrole, see: Williamson, B. L.; Stang, P. J. Synlett 1992, 199-200.
    • (1992) Synlett , pp. 199-200
    • Williamson, B.L.1    Stang, P.J.2
  • 57
  • 60
    • 26844575669 scopus 로고    scopus 로고
    • note
    • See Supporting Information for details.
  • 61
    • 0000418343 scopus 로고    scopus 로고
    • For a discussion on the competitive loss of triflates via nucleophilic attack at the sulfur center during N-arylation of amines with electron-deficient aryl triflates, see: (a) Wolfe, J. P.; Buchwald, S. L. J. Org. Chem. 1997, 62, 1264-1267.
    • (1997) J. Org. Chem. , vol.62 , pp. 1264-1267
    • Wolfe, J.P.1    Buchwald, S.L.2
  • 63
    • 26844493116 scopus 로고    scopus 로고
    • note
    • For a discussion on the rate of reductive elimination and C-N bond formation in N-arylation of azaheterocycles, see ref 2c.
  • 64
    • 26844494625 scopus 로고    scopus 로고
    • note
    • The immediate heating of the starting reaction components to temperatures above 60 °C is not recommended. In the case of triflate 5a, omission of this incubation time resulted in a noticeable decrease in the efficiency of the coupling reaction.
  • 65
    • 26844505240 scopus 로고    scopus 로고
    • note
    • n-palladium complexes due to higher concentration of the aza-anion may also be in part responsible for the observed lower reactivity of acidic azaheterocycles; see ref 2c.
  • 66
    • 26844569238 scopus 로고    scopus 로고
    • note
    • The ease of stereospecific synthesis of fully substituted vinyl triflates as compared to the corresponding vinyl iodides is noteworthy; see refs 8-10.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.