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Volumn 67, Issue 26, 2002, Pages 9276-9287

Carbopalladation of nitriles: Synthesis of 2,3-diarylindenones and polycyclic aromatic ketones by the Pd-catalyzed annulation of alkynes and bicyclic alkenes by 2-iodoarenenitriles

Author keywords

[No Author keywords available]

Indexed keywords

CARBOPALLADATION; YIELDS;

EID: 0037184766     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026178g     Document Type: Article
Times cited : (172)

References (86)
  • 9
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    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • (b) Soderberg, B. C. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 241.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 241
    • Soderberg, B.C.1
  • 22
    • 0000322361 scopus 로고
    • For an example of the solvent nitrile incorporation into the product without involving carbopalladation of the cyano group, see: Hegedus, L. S.; Mulhern, T. A.; Asada, H. J. Am. Chem. Soc. 1986, 108, 6224.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 6224
    • Hegedus, L.S.1    Mulhern, T.A.2    Asada, H.3
  • 62
    • 0034614049 scopus 로고    scopus 로고
    • The exact opposite process, β-carbon elimination from a strained cyclobutaniminopalladium complex to produce a γ-cyanoalkylpalladium species, has been reported: Nishimura, T.; Uemura, S. J. Am. Chem. Soc. 2000, 122, 12049.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 12049
    • Nishimura, T.1    Uemura, S.2
  • 67
    • 0030031026 scopus 로고    scopus 로고
    • and references therein
    • (a) Tsuji, J.; Mandai, T. Synthesis 1996, 1 and references therein.
    • (1996) Synthesis , pp. 1
    • Tsuji, J.1    Mandai, T.2
  • 74
    • 0346522055 scopus 로고    scopus 로고
    • note
    • 2O and our intermediate C can explain the formation of deuterium-containing products in ref 31b without involving β-C-H bond activation.
  • 77
    • 0035833048 scopus 로고    scopus 로고
    • and references therein
    • 1H NMR spectroscopic methods of assigning the stereochemistry of bicyclic systems, see: Mayo, P.; Tam, W. Tetrahedron 2001, 57, 5943 and references therein.
    • (2001) Tetrahedron , vol.57 , pp. 5943
    • Mayo, P.1    Tam, W.2
  • 81
    • 0001729405 scopus 로고
    • Trost, B. M., Ed.; Pergamon Press: New York; Chapter 21
    • Gawley, R. E.; Rein, K. In Comprehensive Organic Synthesis; Trost, B. M., Ed.; Pergamon Press: New York, 1991; Vol. 1, Chapter 2.1, pp 461 and 468.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 461
    • Gawley, R.E.1    Rein, K.2
  • 85
    • 0346522053 scopus 로고    scopus 로고
    • note
    • This model can also account for the results we have obtained in the attempted annulation of diphenylacetylene by 2-bromobenzonitrile (30% yield of 1 with 80% conversion of the starting material after 72 h) and 2-cyanophenyl triflate (no annulation product). The annulation is probably impeded since the Pd-Br bond in IIIa (X = Br) would reduce the partial negative charge on the vinylic carbon due to bromine's relatively high electronegativity, and palladium triflates (IIIa, X = OTf) are known to easily dissociate and form cationic palladium complexes, obviously incapable of nucleophilic reactions.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.