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Volumn 128, Issue 25, 2006, Pages 8146-8147

Hydroheteroarylation of alkynes under mild nickel catalysis

Author keywords

[No Author keywords available]

Indexed keywords

3 CYANOINDOLE; 4 OCTYNE; ALKYNE; INDOLE DERIVATIVE; NICKEL; UNCLASSIFIED DRUG;

EID: 33745660522     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0623459     Document Type: Article
Times cited : (245)

References (63)
  • 1
    • 33947488258 scopus 로고
    • For rare examples of stoichiometric and catalytic C-H activation by nickel, see: (a) Kleiman, J. P.; Dubeck, M. J. Am. Chem. Soc. 1963, 85, 1544.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 1544
    • Kleiman, J.P.1    Dubeck, M.2
  • 8
    • 7444242751 scopus 로고    scopus 로고
    • For ligand-dependent divergent nickel catalysis on the reactions of benzonitrile with alkynes, see: (a) Nakao, Y.; Oda, S.; Hiyama, T. J. Am. Chem. Soc. 2004, 126, 13904.
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 13904
    • Nakao, Y.1    Oda, S.2    Hiyama, T.3
  • 11
    • 33745644106 scopus 로고    scopus 로고
    • note
    • A stereochemically unidentified product derived from the insertion of two molecules of 2a into the Ar-H bond at the C-2 position of 1b was also obtained in 31% yield.
  • 12
    • 33745646826 scopus 로고    scopus 로고
    • note
    • 3 were found totally ineffective for the present hydroarylation.
  • 13
    • 33745647946 scopus 로고    scopus 로고
    • note
    • 2 in the absence of an alkyne; see also ref 1f.
  • 14
    • 33745641972 scopus 로고    scopus 로고
    • note
    • 1.
  • 15
    • 33745678583 scopus 로고    scopus 로고
    • note
    • 1 and methyl 1-methylindole-3-carboxylate (1c) with 2a (1.0 mmol) under the identical conditions did not cause intermolecular deuterium crossover.
  • 16
    • 33745676168 scopus 로고    scopus 로고
    • note
    • 3. (Diagram presented)
  • 20
    • 33745642191 scopus 로고    scopus 로고
    • note
    • Similar regiochemistry was also reported for hydronickelation of unsymmetrical alkynes; see entries 16-18 of Table 2 and refs 1b and If.
  • 21
    • 0003112681 scopus 로고
    • For representative examples of cis-hydroarylation of alkynes via oxidative addition of an Ar-H bond at high temperature or under irradiation, see: (a) Hong, P.; Cho, B.-R.; Yamazaki, H. Chem. Lett. 1979, 339.
    • (1979) Chem. Lett. , pp. 339
    • Hong, P.1    Cho, B.-R.2    Yamazaki, H.3
  • 32
    • 33745641758 scopus 로고    scopus 로고
    • note
    • At present, the following (hetero)arenes have failed to participate in the reaction: 4-(trifluoromethyl)benzonitrile, methyl 4-(trifluoromethyl)ben- zoatc, ethyl 1-methylindole-2-carboxylate, 1-methylpyrrole, 1-methyl imidazole. Unsubstituted indoles gave a mixture of 2- and 3-alkenylated products.
  • 33
    • 33745678127 scopus 로고    scopus 로고
    • note
    • 3), catalyst at 115 °C has been reported to give the corresponding adduct as a mixture of stereoisomers in 42% yield; see ref 9f.
  • 34
    • 33745679026 scopus 로고    scopus 로고
    • note
    • Terminal alkynes failed to give the corresponding adducts due to rapid background oligomerization of alkynes.
  • 35
    • 0003071359 scopus 로고
    • For selected examples of related hydroheteroarylations of unsaturated bonds, see: (a) Hong, P.; Cho, B.-R.; Yamazaki, H. Chem. Lett. 1980, 507.
    • (1980) Chem. Lett. , pp. 507
    • Hong, P.1    Cho, B.-R.2    Yamazaki, H.3
  • 52
    • 0037872649 scopus 로고    scopus 로고
    • For selected recent work on intermolecular transition-metal-catalyzed C-C bond formation of indoles via C-H activation, see: (a) Sawada, T.; Fuerst, D. E.; Wood, J. L. Tetrahedron Lett. 2003, 44, 4919.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 4919
    • Sawada, T.1    Fuerst, D.E.2    Wood, J.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.