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Volumn , Issue 8, 2006, Pages 894-896

Palladium-catalyzed carbopalladation and carbocyclization of arynes with aryl halides: A highly efficient route to functionalized triphenylenes

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE DERIVATIVE; ALKYNE DERIVATIVE; HALIDE; PALLADIUM;

EID: 32844456016     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/b515846j     Document Type: Article
Times cited : (67)

References (30)
  • 1
    • 84941906616 scopus 로고
    • For a brief review of discotics, see: (a) S. Chandrasekhar, Liq. Cryst., 1993, 14, 3;
    • (1993) Liq. Cryst. , vol.14 , pp. 3
    • Chandrasekhar, S.1
  • 20
    • 32844467301 scopus 로고    scopus 로고
    • note
    • 3CN is the most common and suitable reagent used to generate arynes from their precursor 2-(trimethylsilyl)-phenyl triflates.
  • 21
    • 0001347811 scopus 로고
    • For the palladium-catalyzed reaction of an aryl halide and two alkynes leading to naphthalenes, see: (a) G. Wu, A. L. Rheingold, S. L. Geib and R. F. Heck, Organometallics, 1987, 6, 1941;
    • (1987) Organometallics , vol.6 , pp. 1941
    • Wu, G.1    Rheingold, A.L.2    Geib, S.L.3    Heck, R.F.4
  • 23
    • 27844442610 scopus 로고    scopus 로고
    • Since the completion of this work, an article has appeared which describes a synthesis of triphenylene. According to the single example presented in the paper, aryne 1b reacted with 2b to yield the corresponding triphenylene in only 50% yield. It is noteworthy that our method, utilizing a suitable additive and thereby milder, reproducible conditions, afforded triphenylenes in very good yields. Moreover, aryne 1a was also successfully employed. See: Z. Liu, X. Zhang and R. C. Larock, J. Am. Chem. Soc., 2005, 127, 15716.
    • (2005) J. Am. Chem. Soc. , vol.127 , pp. 15716
    • Liu, Z.1    Zhang, X.2    Larock, R.C.3
  • 24
    • 32844474961 scopus 로고    scopus 로고
    • note
    • Even though there is much precedence for the generation of arynes from precursors 1, we carried out a reaction with an unsymmetrical aryne 4-methyl-2-trimethylsilylaryltriflate with 2a. A mixture of regioisomers, as expected for a reaction of 4-methylbenzyne, was obtained, thereby confirming the involvement of arynes in this reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.