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Volumn 68, Issue 11, 2003, Pages 4457-4463

Preparation of tri- and difluoromethylsilanes via an unusual magnesium metal-mediated reductive tri- and difluoromethylation of chlorosilanes using tri- and difluoromethyl sulfides, sulfoxides, and sulfones

Author keywords

[No Author keywords available]

Indexed keywords

METAL-MEDIATED REDUCTIVES;

EID: 0038441453     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo030110z     Document Type: Article
Times cited : (144)

References (56)
  • 23
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    • Although several different (difluoromethyl)silanes are documented in the literature, their preparations give low yields or need high-cost precursors such as TMS-CF2C1. See reports: (a) Liu, E. K. S.; Lagow, R. J. J. Organomet. Chem. 1978, 145, 167. (b) Broicher, V.; Geffken, D. J. Orgnomet. Chem. 1990, 381, 315. (c) Buerger, H.; Moritz, P. J. Organomet. Chem. 1992, 427, 293. (d) Fuchikami, T.; Ojima, I. J. Organomet. Chem. 1981, 212, 145.
    • (1978) Organomet. Chem. , vol.145 , pp. 167
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  • 24
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    • Although several different (difluoromethyl)silanes are documented in the literature, their preparations give low yields or need high-cost precursors such as TMS-CF2C1. See reports: (a) Liu, E. K. S.; Lagow, R. J. J. Organomet. Chem. 1978, 145, 167. (b) Broicher, V.; Geffken, D. J. Orgnomet. Chem. 1990, 381, 315. (c) Buerger, H.; Moritz, P. J. Organomet. Chem. 1992, 427, 293. (d) Fuchikami, T.; Ojima, I. J. Organomet. Chem. 1981, 212, 145.
    • (1990) Orgnomet. Chem. , vol.381 , pp. 315
    • Broicher, V.1    Geffken, D.J.2
  • 25
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    • Although several different (difluoromethyl)silanes are documented in the literature, their preparations give low yields or need high-cost precursors such as TMS-CF2C1. See reports: (a) Liu, E. K. S.; Lagow, R. J. J. Organomet. Chem. 1978, 145, 167. (b) Broicher, V.; Geffken, D. J. Orgnomet. Chem. 1990, 381, 315. (c) Buerger, H.; Moritz, P. J. Organomet. Chem. 1992, 427, 293. (d) Fuchikami, T.; Ojima, I. J. Organomet. Chem. 1981, 212, 145.
    • (1992) J. Organomet. Chem. , vol.427 , pp. 293
    • Buerger, H.1    Moritz, P.2
  • 26
    • 0010731486 scopus 로고
    • Although several different (difluoromethyl)silanes are documented in the literature, their preparations give low yields or need high-cost precursors such as TMS-CF2C1. See reports: (a) Liu, E. K. S.; Lagow, R. J. J. Organomet. Chem. 1978, 145, 167. (b) Broicher, V.; Geffken, D. J. Orgnomet. Chem. 1990, 381, 315. (c) Buerger, H.; Moritz, P. J. Organomet. Chem. 1992, 427, 293. (d) Fuchikami, T.; Ojima, I. J. Organomet. Chem. 1981, 212, 145.
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  • 35
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    • Trifluoromethyl phenyl sulfide, sulfoxide, and sulphone are all commercially available. A number of reports on their preparation have appeared in the literature. For recent reports, see: (a) Russell, J.; Roques, N. Tetrahedron 1998, 54, 13771. (b) Gerard, F.; Jean-Mannel, M.; Laurent, S.-J. Eur. Pat. Appl. 1996, EP 733614, 13 pp. (c) Chen, Q.-Y.; Duan, J.-X. Chem. Commun. 1993, 918. (d) Yang, J.-J.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1998, 63, 2656.
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    • Eur. Pat. Appl. 1996, EP 733614, 13 pp
    • Trifluoromethyl phenyl sulfide, sulfoxide, and sulphone are all commercially available. A number of reports on their preparation have appeared in the literature. For recent reports, see: (a) Russell, J.; Roques, N. Tetrahedron 1998, 54, 13771. (b) Gerard, F.; Jean-Mannel, M.; Laurent, S.-J. Eur. Pat. Appl. 1996, EP 733614, 13 pp. (c) Chen, Q.-Y.; Duan, J.-X. Chem. Commun. 1993, 918. (d) Yang, J.-J.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1998, 63, 2656.
    • Gerard, F.1    Jean-Mannel, M.2    Laurent, S.-J.3
  • 37
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    • Trifluoromethyl phenyl sulfide, sulfoxide, and sulphone are all commercially available. A number of reports on their preparation have appeared in the literature. For recent reports, see: (a) Russell, J.; Roques, N. Tetrahedron 1998, 54, 13771. (b) Gerard, F.; Jean-Mannel, M.; Laurent, S.-J. Eur. Pat. Appl. 1996, EP 733614, 13 pp. (c) Chen, Q.-Y.; Duan, J.-X. Chem. Commun. 1993, 918. (d) Yang, J.-J.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1998, 63, 2656.
    • (1993) Chem. Commun. , pp. 918
    • Chen, Q.-Y.1    Duan, J.-X.2
  • 38
    • 0000540418 scopus 로고    scopus 로고
    • Trifluoromethyl phenyl sulfide, sulfoxide, and sulphone are all commercially available. A number of reports on their preparation have appeared in the literature. For recent reports, see: (a) Russell, J.; Roques, N. Tetrahedron 1998, 54, 13771. (b) Gerard, F.; Jean-Mannel, M.; Laurent, S.-J. Eur. Pat. Appl. 1996, EP 733614, 13 pp. (c) Chen, Q.-Y.; Duan, J.-X. Chem. Commun. 1993, 918. (d) Yang, J.-J.; Kirchmeier, R. L.; Shreeve, J. M. J. Org. Chem. 1998, 63, 2656.
    • (1998) J. Org. Chem. , vol.63 , pp. 2656
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  • 42
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    • note
    • Commercial magnesium turnings were used without special pretreatment.
  • 43
  • 44
    • 0038728789 scopus 로고    scopus 로고
    • note
    • 3 and PhS
  • 45
    • 0038728790 scopus 로고    scopus 로고
    • note
    • 3H and PhSSPh. See ref 15.
  • 53
    • 0038390643 scopus 로고    scopus 로고
    • Jpn. Kokai Tokkyo Koho 2001, JP 2001039942
    • Yamamoto, T.; Watanabe, H. Jpn. Kokai Tokkyo Koho 2001, JP 2001039942.
    • Yamamoto, T.1    Watanabe, H.2
  • 55
  • 56
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    • note
    • 3H) is not currently banned. However, it is known that this compound may have relatively high potential to cause greenhouse warming.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.