Synthesis of propargylic fluorides from allenylsilanes

被引:28
作者
Carroll, Laurence [1 ]
Pacheco, Ma Carmen [1 ]
Garcia, Ludivine [1 ]
Gouverneur, Veronique [1 ]
机构
[1] Univ Oxford, Chem Res Lab, Oxford OX1 3TA, England
关键词
D O I
10.1039/b610013a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Allenylsilanes reacted at room temperature in acetonitrile with Selectfluor, an electrophilic fluorinating reagent, to give secondary propargylic fluorides in moderate to good yields; mechanistically, a side-product resulting from a 1,2-silyl shift testifies to the presence of a cationic intermediate.
引用
收藏
页码:4113 / 4115
页数:3
相关论文
共 28 条
[1]  
BROOK AG, 1980, REARRANGEMENTS GROUN, V2, P190
[2]  
De Jonghe S, 2000, EUR J ORG CHEM, V2000, P3177
[3]   High regio- and stereocontrol in the dehydroxy-fluorination of propargylic alcohols and the corresponding cobalt-carbonyl complexes [J].
Grée, D ;
Madiot, V ;
Grée, R .
TETRAHEDRON LETTERS, 1999, 40 (35) :6399-6402
[4]   Mechanism-based inactivation of thymidylate synthase by 5-(3-fluoropropyn-1-yl)-2′-deoxyuridine 5′-phosphate [J].
Kalman, TI ;
Nie, Z ;
Kamat, A .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2000, 10 (04) :391-394
[5]   4-FLUORO-2-BUTYNAL - PREPARATION AND SOME EXAMPLES OF DIENOPHILIC PROPERTIES [J].
KHANOUS, A ;
GORGUES, A ;
COUSSEAU, J .
JOURNAL OF FLUORINE CHEMISTRY, 1990, 49 (03) :401-408
[6]  
KIRSCH P, 2006, MODERN FLUOROORGANIC, V34, P277
[7]  
Kornilov A. M, 1989, J ORG CHEM USSR, V25, P2260
[8]   A new metal mediated stereocontrolled synthesis of allylic fluorides [J].
Madiot, V ;
Grée, D ;
Grée, R .
TETRAHEDRON LETTERS, 1999, 40 (35) :6403-6406
[9]   Highly enantioselective propargylic monofluorination established by carbon-13 and fluorine-19 NMR in chiral liquid crystals [J].
Madiot, V ;
Lesot, P ;
Grée, D ;
Courtieu, J ;
Gree, R .
CHEMICAL COMMUNICATIONS, 2000, (02) :169-170
[10]   DIASTEREOSELECTIVE REACTIONS OF CHIRAL ALLYLSILANES AND ALLENYLSILANES WITH ACTIVATED C-X PI-BONDS [J].
MASSE, CE ;
PANEK, JS .
CHEMICAL REVIEWS, 1995, 95 (05) :1293-1316