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Volumn 66, Issue 32, 2010, Pages 5993-5999

Silver-catalyzed coupling reactions of alkyl halides with indenyllithiums

Author keywords

Alkyl halide; Carbon Carbon bond formation; Coupling reaction; Silver

Indexed keywords

1 (1 ADAMANTYL) 1H INDENE; 1 (1 METHYL 3 PHENYLPROPYL) 1H INDENE; 1 (1,1 DIMETHYLETHYL) 1H INDENE; 1 (1,1 DIMETHYLNONYL) 1H INDENE; 1 [1 METHYL 4 (1,1 DIMETHYLETHYL)CYCLOHEXYL] 1H INDENE; 1 [3 (4 BROMOPHENYL) 1 METHYLPROPYL) 1H INDENE; 1 CYCLOHEXYL 1H INDENE; 1,3 DIALKYLINDENE DERIVATIVE; 1H,1H' 1,1' BIINDENE; 2 [[10 (1H INDEN 1 YL)UNDECYL]OXY]TETRAHYDROPYRAN; 3 (1,1 DIMETHYLNONYL) 1 (1 METHYL 3 PHENYLPROPYL) 1H INDENE; 3 (1,1 DIMETHYLNONYL) 1 (1,1 DIMETHYL 3 PHENYLPROPYL) 1H INDENE; 3 (1,1 DIMETHYLNONYL) 1 TRIMETHYLSILYL 1H INDENE; 3 BROMO 1 (4 BROMOPHENYL)BUTANE; 3 BROMO 3 METHYL 1 PHENYLBUTANE; 3 CHLORO 3 METHYL 1 PHENYLBUTANE; 9 (1 METHYL 3 PHENYLPROPYL) 9H FLUORENE; 9 (1,1 DIMETHYL 3 PHENYLPROPYL) 9H FLUORENE; ALKYLHALIDE DERIVATIVE; HALIDE; INDENE DERIVATIVE; INDENYLLITHIUM DERIVATIVE; LITHIUM DERIVATIVE; N [10 (1H INDEN 1 YL)UNDECYL] N (PHENYLMETHYL) 4 METHYLBENZENESULFONAMIDE; SILVER; UNCLASSIFIED DRUG;

EID: 77955425575     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.06.030     Document Type: Article
Times cited : (26)

References (73)
  • 18
    • 0344861888 scopus 로고    scopus 로고
    • For selected examples
    • For selected examples, see: J. Zhou, and G.C. Fu J. Am. Chem. Soc. 125 2003 14726 14727
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 14726-14727
    • Zhou, J.1    Fu, G.C.2
  • 26
    • 0036643455 scopus 로고    scopus 로고
    • For examples of transition-metal-catalyzed coupling reactions with organolithiums
    • For examples of transition-metal-catalyzed coupling reactions with organolithiums, see: S.-I. Murahashi J. Organomet. Chem. 653 2002 27 33
    • (2002) J. Organomet. Chem. , vol.653 , pp. 27-33
    • Murahashi, S.-I.1
  • 34
    • 0006790099 scopus 로고
    • Silver-catalyzed reactions of alkyl halides with organometallic reagents reported by other groups
    • Silver-catalyzed reactions of alkyl halides with organometallic reagents reported by other groups: M. Tamura, and J.K. Kochi Bull. Chem. Soc. Jpn. 45 1972 1120 1127
    • (1972) Bull. Chem. Soc. Jpn. , vol.45 , pp. 1120-1127
    • Tamura, M.1    Kochi, J.K.2
  • 45
    • 77955429871 scopus 로고    scopus 로고
    • Note
    • When the catalytic amount of AgBr was reduced from 5 mol %, a prolonged reaction time was needed. Reoptimization of the reaction time should be required.
  • 46
    • 77955425225 scopus 로고    scopus 로고
    • Note
    • The silver-catalyzed reactions with indenylmagnesium bromide/LiBr complex and with indenyllithium/TMEDA complex afforded 2a in 37% and 9% yields, respectively.
  • 47
    • 84943966160 scopus 로고
    • The uncatalyzed reaction of tert-butyl chloride with indenyllithium could afford 2d in low yield: L. Cedheim, and L. Eberson Synthesis 1973 159
    • (1973) Synthesis , pp. 159
    • Cedheim, L.1    Eberson, L.2
  • 48
    • 77955421811 scopus 로고    scopus 로고
    • The coupling reaction of 1a without AgBr was so slow that alkene rather than the desired coupling product was gradually produced by elimination.
    • The coupling reaction of 1a without AgBr was so slow that alkene rather than the desired coupling product was gradually produced by elimination.
  • 49
    • 77955422656 scopus 로고    scopus 로고
    • Note
    • 2O are important.
  • 50
    • 77955416266 scopus 로고    scopus 로고
    • Note
    • In each case, indene was recovered by the protonation of the unreacted indenyllithium after the work-up.
  • 51
    • 77955415946 scopus 로고    scopus 로고
    • The reaction of 1f without AgBr afforded 2e in 28% yield
    • The reaction of 1f without AgBr afforded 2e in 28% yield.
  • 57
    • 77955418827 scopus 로고    scopus 로고
    • Note
    • 1H NMR spectrum of 6 with those of 2a, 2e, and 2j.
  • 67
    • 77955423087 scopus 로고    scopus 로고
    • Note
    • The results of entries 4 and 5 in Table 2 indicate that single electron process (B) is the rate-limiting step in this reaction.
  • 69
    • 0001423263 scopus 로고
    • Cyclopentadienylsilver(I) complexes are known
    • Cyclopentadienylsilver(I) complexes are known: C. Zybill, and G. Müller Organometallics 6 1987 2489 2494
    • (1987) Organometallics , vol.6 , pp. 2489-2494
    • Zybill, C.1    Müller, G.2
  • 73
    • 77955413522 scopus 로고    scopus 로고
    • Note
    • The stereochemistry of the products was tentatively assigned in analogy with the corresponding alkylated products. The alkylated products were reported in Ref. 3b and 27.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.