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Volumn 13, Issue 5, 2011, Pages 956-959

Copper-free Sonogashira coupling of cyclopropyl iodides with terminal alkynes

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; COPPER; CYCLOPROPANE DERIVATIVE; IODINATED HYDROCARBON; PALLADIUM;

EID: 79952151268     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol1029996     Document Type: Article
Times cited : (34)

References (77)
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  • 17
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    • For an efficient synthesis of cyclopropyl Grignard reagents, see:;;; Angew. Chem., Int. Ed. 2002, 41, 351-352
    • Limmert, M. E.; Roy, A. H.; Hartwig, J. F. J. Org. Chem. 2005, 70, 9364-9370 For an efficient synthesis of cyclopropyl Grignard reagents, see: Vu, V. A.; Marek, I.; Polborn, K.; Knochel, P. Angew. Chem., Int. Ed. 2002, 41, 351-352
    • (2005) J. Org. Chem. , vol.70 , pp. 9364-9370
    • Limmert, M.E.1    Roy, A.H.2    Hartwig, J.F.3    Vu, V.A.4    Marek, I.5    Polborn, K.6    Knochel, P.7
  • 39
    • 77950268669 scopus 로고    scopus 로고
    • For application of these cross-coupling reactions in the synthesis of arylcyclopropanes
    • For application of these cross-coupling reactions in the synthesis of arylcyclopropanes, see: Gagnon, A.; Duplessis, M.; Fader, L. Org. Prep. Proc. Intl. 2010, 42, 1-69
    • (2010) Org. Prep. Proc. Intl. , vol.42 , pp. 1-69
    • Gagnon, A.1    Duplessis, M.2    Fader, L.3
  • 41
    • 0000264260 scopus 로고    scopus 로고
    • Formation of cyclopropyllithium species by lithium-halogen exchange also illustrates this property; see:;; J. Am. Chem. Soc. 1964, 86, 3283-3288
    • Wiberg, K. B. Acc. Chem. Res. 1996, 29, 229-234 Formation of cyclopropyllithium species by lithium-halogen exchange also illustrates this property; see: Walborsky, B. H.; Impastato, F. J.; Young, A. E. J. Am. Chem. Soc. 1964, 86, 3283-3288
    • (1996) Acc. Chem. Res. , vol.29 , pp. 229-234
    • Wiberg, K.B.1    Walborsky, B.H.2    Impastato, F.J.3    Young, A.E.4
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    • Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim,; pp -239.
    • Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.; Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998; pp 203 -239.
    • (1998) Metal-Catalyzed Cross-Coupling Reactions , pp. 203-239
    • Sonogashira, K.1
  • 65
    • 79952150187 scopus 로고    scopus 로고
    • 3N in toluene or THF (rt to reflux).
    • 3N in toluene or THF (rt to reflux).
  • 70
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    • The Sonogashira reaction of primary alkyl halides (using carbene ligands) has also been reported
    • The Sonogashira reaction of primary alkyl halides (using carbene ligands) has also been reported; see: Eckhardt, M.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 13642-13643
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 13642-13643
    • Eckhardt, M.1    Fu, G.C.2
  • 71
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    • 3P led to much lower conversions. BINAP, XantPhos, and dppf were unsuitable.
    • 3P led to much lower conversions. BINAP, XantPhos, and dppf were unsuitable.
  • 72
    • 33846232311 scopus 로고    scopus 로고
    • For mechanistic investigations on the so-called copper-free Sonogashira coupling
    • For mechanistic investigations on the so-called copper-free Sonogashira coupling, see: Tougerti, A.; Negri, S.; Jutand, A. Chem.-Eur. J. 2007, 13, 666-676
    • (2007) Chem.-Eur. J. , vol.13 , pp. 666-676
    • Tougerti, A.1    Negri, S.2    Jutand, A.3
  • 75
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    • 3 J coupling constants between the cyclopropyl protons; see the Supporting Information for details. Comparison of the spectra of the cis -cyclopropanemethanols 2, 4, 5 and their corresponding trans diastereomers 20, 21, 22, respectively, also confirmed the results unambiguously.
    • 3 J coupling constants between the cyclopropyl protons; see the Supporting Information for details. Comparison of the spectra of the cis -cyclopropanemethanols 2, 4, 5 and their corresponding trans diastereomers 20, 21, 22, respectively, also confirmed the results unambiguously.
  • 76
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    • Competitive consumption of aryl alkynes in slow copper-free Sonogashira coupling has already been observed as a side reaction under similar conditions; see ref 19.
    • Competitive consumption of aryl alkynes in slow copper-free Sonogashira coupling has already been observed as a side reaction under similar conditions; see ref 19.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.