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Volumn 126, Issue 1, 2004, Pages 320-328

Rhodium-Catalyzed Methylenation of Aldehydes

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; OLEFINS; OPTIMIZATION; RHODIUM; SPECTROSCOPIC ANALYSIS;

EID: 0345868445     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja038112o     Document Type: Article
Times cited : (97)

References (156)
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    • (1991) Alkene Synthesis , vol.1 , pp. 729
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    • 0000308093 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Comprehensive Organometallic Chemistry 11: Pergamon: Oxford, U.K.
    • (b) Stille, J. R. In Transition Metal Carbene Complexes: Tebbe's Reagent and Related Nacleophilic Alkylidenes; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Comprehensive Organometallic Chemistry 11: Pergamon: Oxford, U.K., 1995; Vol. 12, pp 577-600.
    • (1995) Transition Metal Carbene Complexes: Tebbe's Reagent and Related Nacleophilic Alkylidenes , vol.12 , pp. 577-600
    • Stille, J.R.1
  • 23
  • 47
    • 0034801829 scopus 로고    scopus 로고
    • In the absence of the phosphine and alcohol reagents, the formation of silyl enol ethers was reported with aromatic aldehydes under similar reaction conditions; see: (a) Dias, E. L.; Brookhart, M.; White, P. S. J. Am. Chem. Soc. 2001, 123, 2442-2443.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 2442-2443
    • Dias, E.L.1    Brookhart, M.2    White, P.S.3
  • 49
    • 0042170073 scopus 로고    scopus 로고
    • For a very recent application of methyltrioxorhenium-catalyzed olefination of a diazo-amide that provides the corresponding alkene in poor to moderate yields, see: Harrison, R.; Mete, A.; Wilson, L. Tetrahedron Lett. 2003, 44, 6621-6624.
    • (2003) Tetrahedron Lett. , vol.44 , pp. 6621-6624
    • Harrison, R.1    Mete, A.2    Wilson, L.3
  • 84
    • 4243335224 scopus 로고
    • U.S. Patent 3,865,848, 1975
    • (a) Nysted, L. N. U.S. Patent 3,865,848, 1975; Chem. Abstr. 1975, 83, 1-406q.
    • (1975) Chem. Abstr. , vol.83
    • Nysted, L.N.1
  • 92
    • 0347494859 scopus 로고    scopus 로고
    • For stoichiometric molybdenum and tungsten reagents, see: (a) Kauffmann, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 1259-1275.
    • (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 1259-1275
    • Kauffmann, T.1
  • 102
    • 85039587033 scopus 로고    scopus 로고
    • note
    • Due to solubility issues, it is required to use rhodium(III) chloride hydrate (instead of rhodium(III) chloride anhydrous) to prepare the chlorotris(triphenyl phosphine)rhodium(I).
  • 109
    • 85039586949 scopus 로고    scopus 로고
    • note
    • The reaction is tolerant toward a certain amount of water, and up to 1 equiv of water could be added to the reaction mixture without affecting the yield. However, the addition of 5 equiv of water completely inhibits the methylenation reaction.
  • 124
    • 85039586507 scopus 로고    scopus 로고
    • note
    • As trimethylsilyldiazomethane is nonexplosive and nonmutagenic, the very careful operations used for the preparation of diazomethane are not necessary.
  • 125
    • 33845550147 scopus 로고
    • A number of polymer-supported triphenylphosphine reagents have been developed to overcome this problem: (a) Bernard, M.; Ford, W. T. J. Org. Chem. 1983, 48, 326-332.
    • (1983) J. Org. Chem. , vol.48 , pp. 326-332
    • Bernard, M.1    Ford, W.T.2
  • 131
    • 85039579991 scopus 로고    scopus 로고
    • note
    • If necessary, it is possible to avoid the use of TBAF, by performing a hydrolysis under basic conditions or a cleavage using strong acid, such as trifluoroacetic acid. See ref 41.
  • 152
    • 85039579702 scopus 로고    scopus 로고
    • note
    • We suggest the formation of a rhodium(I) complex with trimelhylsilyldiazomethane that has a similar coordination to that observed by Brookhart; see ref 16.
  • 155
    • 85039575676 scopus 로고    scopus 로고
    • note
    • All of the alcohols were purified under drying agents prior to use, although we have shown that the methylenation reaction is not strongly influenced by the presence of water; see ref 35.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.