Boron trifluoride-mediated alkylation of diphenylphosphine with tert-alkyl fluoride

被引:36
作者
Hirano, K [1 ]
Yorimitsu, H [1 ]
Oshima, K [1 ]
机构
[1] Kyoto Univ, Grad Sch Engn, Dept Chem Mat, Nishikyo Ku, Kyoto 6158510, Japan
关键词
D O I
10.1021/ol048069p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[Graphic] Treatment of tertiary alkyl fluoride with diphenylphosphine in the presence of a stoichiometric amount of boron trifluoride etherate yields the corresponding tert-alkyldiphenylphosphine despite the coexistence of the strong Lewis acid and the highly coordinating phosphine. Use of diphenyl(trimethylsilyl)phosphine as a nucleophile makes the reaction catalytic in boron trifluoride.
引用
收藏
页码:4873 / 4875
页数:3
相关论文
共 21 条
[1]   FREE-RADICAL CATALYZED ADDITIONS TO THE DOUBLE-BOND OF DIKETENE - A SYNTHESIS OF NOVEL OXETAN-2-ONES [J].
DINGWALL, JG ;
TUCK, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1986, (12) :2081-2090
[2]  
ELSNER G, 1982, METHODEN ORGANISCH E, V1, P106
[3]   THE RELATIVE STABILITIES OF SOME MOLECULAR ADDITION COMPOUNDS OF BORON [J].
GRAHAM, WAG ;
STONE, FGA .
JOURNAL OF INORGANIC & NUCLEAR CHEMISTRY, 1956, 3 (3-4) :164-177
[4]   Boron trifluoride-catalyzed reaction of alkyl fluoride with silyl enolate, allylsilane, and hydrosilane [J].
Hirano, K ;
Fujita, K ;
Yorimitsu, H ;
Shinokubo, H ;
Oshima, K .
TETRAHEDRON LETTERS, 2004, 45 (12) :2555-2557
[5]   DARSTELLUNG UND EIGENSCHAFTEN EINIGER PHOSPHORVERBINDUNGEN MIT TERT-BUTYLGRUPPEN [J].
HOFFMANN, H ;
SCHELLEN.P .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (04) :1134-&
[6]   SYNTHESIS AND REACTIONS OF NEW PHOSPHINE BORANES [J].
IMAMOTO, T .
PURE AND APPLIED CHEMISTRY, 1993, 65 (04) :655-660
[7]  
KAWASHIMA T, 1992, 4 SERIES EXPT CHEM, V24, P229
[8]  
Littke AF, 2002, ANGEW CHEM INT EDIT, V41, P4176, DOI 10.1002/1521-3773(20021115)41:22<4176::AID-ANIE4176>3.0.CO
[9]  
2-U
[10]   Air-stable trialkylphosphonium salts: Simple, practical, and versatile replacements for air-sensitive trialkylphosphines. Applications in stoichiometric and catalytic processes [J].
Netherton, MR ;
Fu, GC .
ORGANIC LETTERS, 2001, 3 (26) :4295-4298