Novel generation of 3,3,3-trifluoropropynyllithium and transformation of the carbonyl adducts to trifluoromethyl-substituted allenes

被引：20
作者：
Shimizu, Masaki [1 ]
Higashi, Masahiro [1 ]
Takeda, Youhei [1 ]
Jiang, Guofang [1 ]
Murai, Masahito [1 ]
Hiyama, Tamejiro [1 ]
机构：
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
来源：
SYNLETT | 2007年 / 07期
关键词：
alkynes; allenes; fluorine; lithium; palladium;
D O I：
10.1055/s2007-977422
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A novel method for the generation of 3,3,3-trifluoro-propynyllithium is reported, which involves treatment of trifluoromethyl-substituted enol tosylate, prepared from 1,1-dichloro-3,3,3-trifluoroacetone, with two equivalents of butyllithium. Palladium-catalyzed coupling reaction of sulfonates of the carbonyl adducts with organozinc reagents gave trifluoromethyl-containing tri- and tetrasubstituted allenes.
引用
收藏
页码：1163 / 1165
页数：3
相关论文
共 33 条
  • [1] Banks R.E., 1994, ORGANOFLUORINE CHEM
  • [2] PREPARATION OF TRIFLUOROMETHYL KETONES AND RELATED FLUORINATED KETONES
    BEGUE, JP
    BONNETDELPON, D
    [J]. TETRAHEDRON, 1991, 47 (20-21) : 3207 - 3258
  • [3] POLYHALOGENOALLENES .10. IMPROVED PREPARATION OF PERFLUORO-(3-METHYLBUTA-1,2-DIENE) AND STRUCTURE OF ITS DIMERS
    BOSBURY, PWL
    FIELDS, R
    HASZELDINE, RN
    MORAN, D
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (11): : 1173 - 1177
  • [4] POLYHALOGENOALLENES .11. PREPARATION OF SOME NEW PERFLUORO-1,2-DIENES AND THEIR REACTIONS WITH NUCLEOPHILES
    BOSBURY, PWL
    FIELDS, R
    HASZELDINE, RN
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1978, (05): : 422 - 427
  • [5] Hydrofluorocarbon 245fa: a versatile new synthon in alkyne chemistry
    Brisdon, AK
    Crossley, IR
    [J]. CHEMICAL COMMUNICATIONS, 2002, (20) : 2420 - 2421
  • [6] A FACILE, GENERAL-ROUTE TO PERFLUOROALKYL ALLENES
    BURTON, DJ
    HARTGRAVES, GA
    HSU, J
    [J]. TETRAHEDRON LETTERS, 1990, 31 (26) : 3699 - 3702
  • [7] A facile synthesis of various fluorine-containing indole derivatives via palladium-catalyzed annulation of internal alkynes
    Chae, J
    Konno, T
    Ishihara, T
    Yamanaka, H
    [J]. CHEMISTRY LETTERS, 2004, 33 (03) : 314 - 315
  • [8] PREPARATION AND REACTIONS OF LITHIUM DERIVATIVES OF TRIFLUOROPROPENE AND TRIFLUOROPROPYNE
    DRAKESMI.FG
    STEWART, OJ
    TARRANT, P
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (01) : 280 - &
  • [9] Novel synthesis of 1-aryl-1-trifluoromethylallenes
    Han, HY
    Kim, MS
    Son, JB
    Jeong, IH
    [J]. TETRAHEDRON LETTERS, 2006, 47 (02) : 209 - 212
  • [10] Synthesis and reactions of 1-methyl-5-tributylstannyl-4-trifluoromethylpyrazole
    Hanamoto, Takeshi
    Egashira, Mikio
    Ishizuka, Kentaro
    Furuno, Hiroshi
    Inanaga, Junji
    [J]. TETRAHEDRON, 2006, 62 (26) : 6332 - 6338
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