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Volumn 125, Issue 20, 2003, Pages 6076-6077

A mild C-O bond formation catalyzed by a rhenium-oxo complex

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL; BENZENE DERIVATIVE; CARBON; METAL COMPLEX; OXYGEN; RHENIUM COMPLEX; TERT BUTYL ALCOHOL;

EID: 0037613457     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0343050     Document Type: Article
Times cited : (145)

References (29)
  • 1
    • 0000157513 scopus 로고    scopus 로고
    • 2-C-O bonds of aryl ethers from aryl halides and alcohols, see: (a) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
    • (2002) Top. Curr. Chem. , vol.219 , pp. 131
    • Muci, A.R.1    Buchwald, S.L.2
  • 4
    • 0001940916 scopus 로고
    • Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York
    • Mitsunobu, O. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon Press: New York, 1991: Vol. 6, pp 22-28.
    • (1991) Comprehensive Organic Synthesis , vol.6 , pp. 22-28
    • Mitsunobu, O.1
  • 8
    • 0034676706 scopus 로고    scopus 로고
    • The most widely applied method for the synthesis of propargylic carbon-oxygen bonds relies on a multistep sequence which proceeds through a cobalt stabilized propargylic cation (the Nicholas reaction). (a) Martin, V. S.; Diaz, D. D. Tetrahedron Lett. 2000, 41, 9993.
    • (2000) Tetrahedron Lett. , vol.41 , pp. 9993
    • Martin, V.S.1    Diaz, D.D.2
  • 9
    • 0037140714 scopus 로고    scopus 로고
    • For a review, see: (b) Teobald, B. J. Tetrahedron 2002, 58, 4133.
    • (2002) Tetrahedron , vol.58 , pp. 4133
    • Teobald, B.J.1
  • 18
    • 0035857395 scopus 로고    scopus 로고
    • A vanadium allenolate has been trapped by electrophiles, see: Trost, B. M.; Oi, S. J. Am. Chem. Soc. 2001, 123, 1230.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1230
    • Trost, B.M.1    Oi, S.2
  • 22
    • 0038136276 scopus 로고    scopus 로고
    • note
    • 22(9%):6(59%); THF 2(29%):6(71%); acetone 2(0%):6(53%).
  • 23
    • 0000891720 scopus 로고    scopus 로고
    • Rearrangement by a mechanism involving a rhenium-catalyzed 1,3-oxygen shift (see: Josemon, J.; Espenson, J. H.; Jensen, J. H.; Gordon, M. S. Organometallics 1998, 17, 1835) to generate 1 may be the source of the loss of stereochemistry.
    • (1998) Organometallics , vol.17 , pp. 1835
    • Josemon, J.1    Espenson, J.H.2    Jensen, J.H.3    Gordon, M.S.4
  • 24
    • 84986492906 scopus 로고
    • However, phenylpropargyl cations react with acetonitrile to produce N-propargylamides (Ritter reaction). For an example, see: Nilsson, B. M.; Hacksell, U. J. Heterocycl. Chem. 1989, 26, 269.
    • (1989) J. Heterocycl. Chem. , vol.26 , pp. 269
    • Nilsson, B.M.1    Hacksell, U.2
  • 27
    • 0037798516 scopus 로고    scopus 로고
    • and references therein
    • (b) Han, Y.; Harlan, J.; Stoessel, P.; Frost, B. J.; Norton, J. R.; Miller, S.; Bridgewater, B.; Xu, Q. Inorg. Chem. 2001, 40, 2942. For examples of propargyl-rhenium complexes, see: Casey, C. P.; Chung, S. Inorg. Chim. Acta 2002, 334, 283 and references therein.
    • (2002) Inorg. Chim. Acta , vol.334 , pp. 283
    • Casey, C.P.1    Chung, S.2
  • 28
    • 37049066184 scopus 로고
    • The catalyst is prepared in two steps from commercially available materials and can be stored indefinitely on the bench: (a) Chatt, J.; Rowe, G. A. J. Chem. Soc. 1962, 4019.
    • (1962) J. Chem. Soc. , pp. 4019
    • Chatt, J.1    Rowe, G.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.