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Volumn 65, Issue 34, 2009, Pages 7146-7150

A straightforward copper-free palladium methodology for the selective alkynylation of a wide variety of S-, O-, and N-based mono- and diheterocyclic bromides and chlorides

Author keywords

[No Author keywords available]

Indexed keywords

BENZOTHIAZOLE DERIVATIVE; BROMIDE; CHLORIDE; FURAN DERIVATIVE; HALIDE; HETEROCYCLIC COMPOUND; IONIC LIQUID; NITROGEN; OXYGEN; PALLADIUM; PYRIDAZINE DERIVATIVE; PYRIDINE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINOLINE DERIVATIVE; SOLVENT; SULFUR; THIAZOLE DERIVATIVE; THIOPHENE DERIVATIVE;

EID: 67650607106     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.06.009     Document Type: Article
Times cited : (23)

References (100)
  • 4
    • 67650626270 scopus 로고    scopus 로고
    • For selected representatives examples see
    • For selected representatives examples see:
  • 13
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    • See for an elegant example:
    • See for an elegant example:. Deng X., and Mani N.S. Org. Lett. 8 (2006) 269
    • (2006) Org. Lett. , vol.8 , pp. 269
    • Deng, X.1    Mani, N.S.2
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    • For selected representative examples see
    • For selected representative examples see:
  • 32
    • 67650575552 scopus 로고    scopus 로고
    • For selected representatives examples see
    • For selected representatives examples see:
  • 46
    • 67650575553 scopus 로고    scopus 로고
    • For selected representatives examples see
    • For selected representatives examples see:
  • 58
    • 67650606618 scopus 로고    scopus 로고
    • Efficient methodologies tested on a large variety of heteroaromatics are very scarce and employ sophisticated ligands and/or copper co-catalyst, see
    • Efficient methodologies tested on a large variety of heteroaromatics are very scarce and employ sophisticated ligands and/or copper co-catalyst, see:
  • 66
    • 67650623974 scopus 로고    scopus 로고
    • note
    • 2 €/mol, from small-scale commercial sources (Sigma-Aldrich 2009 lowest prices).
  • 79
    • 67650626263 scopus 로고    scopus 로고
    • note
    • 4] is among the three cheapest ILs sold by Iolitec from a library of 500 ionic liquids of all current classes.
  • 80
    • 67650593483 scopus 로고    scopus 로고
    • Relevant examples are described
    • Relevant examples are described:
  • 87
    • 67650647058 scopus 로고    scopus 로고
    • note
    • See GC and mass spectrum in Supplementary data.
  • 88
    • 67650584077 scopus 로고    scopus 로고
    • note
    • In Ref. 7e this coupling of 3-bromoquinoline is specially tricky (23% yield of 3-(phenylethynyl)quinoline in 24 h at 130 °C).
  • 89
    • 67650600487 scopus 로고    scopus 로고
    • In Ref. 7f the alkynylation of 3-bromofuran with the activated TMSacetylene from Pd/PPh3 in TMEDA as base and solvent in the presence of CuI is problematic 65% yield in 20 h at 80 °C
    • 3 in TMEDA as base and solvent in the presence of CuI is problematic (65% yield in 20 h at 80 °C).
  • 90
    • 67650613832 scopus 로고    scopus 로고
    • Most often 2-halothiophenes couplings are reported, in Ref. 7b is underlined that 3-halothiophenes are more challenging susbtrates since, as electron-excessive heterocycles, thiophenes are more sensitive to halogen position.
    • Most often 2-halothiophenes couplings are reported, in Ref. 7b is underlined that 3-halothiophenes are more challenging susbtrates since, as electron-excessive heterocycles, thiophenes are more sensitive to halogen position.
  • 91
    • 67650581050 scopus 로고    scopus 로고
    • note
    • 2.
  • 92
    • 67650630095 scopus 로고    scopus 로고
    • PCT Int. Appl, WO 2005044814, according to this report dihydro-2H-[1,5]benzodioxepin derivatives would be useful as inhibitors of human acetyl-coenzyme A carboxylase ACC, and stimulate fatty acid oxidation in liver and muscle, which might make them suitable as drugs for diabetes, obesity and dyslipidemia
    • Gobbi, L. C.; Gubler, M.; Neidhart, W.; Nettekoven, M. H. PCT Int. Appl., WO 2005044814, 2005, according to this report dihydro-2H-[1,5]benzodioxepin derivatives would be useful as inhibitors of human acetyl-coenzyme A carboxylase (ACC), and stimulate fatty acid oxidation in liver and muscle, which might make them suitable as drugs for diabetes, obesity and dyslipidemia.
    • (2005)
    • Gobbi, L.C.1    Gubler, M.2    Neidhart, W.3    Nettekoven, M.H.4
  • 94
    • 67650584076 scopus 로고    scopus 로고
    • 4NBr gives only moderate yields of (phenylethynyl)-diheteroaromatics from bromides (43% from 2-Br-thiazole, 46% from 2-Br-pyrimidine, 48% from 2-Br-pyrazine) or from some heteroaromatic chlorides (19% from 2-Cl-pyridine), showing the challenges related to these couplings
    • 4NBr gives only moderate yields of (phenylethynyl)-diheteroaromatics from bromides (43% from 2-Br-thiazole, 46% from 2-Br-pyrimidine, 48% from 2-Br-pyrazine) or from some heteroaromatic chlorides (19% from 2-Cl-pyridine), showing the challenges related to these couplings
  • 95
    • 0035914607 scopus 로고    scopus 로고
    • From 2-iodobenzothiazole only a 41% yield was reported for this reaction with Pd/CuI:
    • From 2-iodobenzothiazole only a 41% yield was reported for this reaction with Pd/CuI:. Kumar D., David W.M., and Kerwin S.M. Bioorg. Med. Chem. Lett. 11 (2001) 2971
    • (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2971
    • Kumar, D.1    David, W.M.2    Kerwin, S.M.3
  • 96
    • 67650585740 scopus 로고    scopus 로고
    • No system was reported, up to now, for this synthesis from aryl chloride in the absence of Cu, and only moderate yield was obtained
    • No system was reported, up to now, for this synthesis from aryl chloride in the absence of Cu, and only moderate yield was obtained:


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.