Indium-mediated reaction of 3-bromo-3,3-difluoropropene and bromodifluoromethylacetylene derivatives with aldehydes

被引:53
作者
Kirihara, M [1 ]
Takuwa, T [1 ]
Takizawa, S [1 ]
Momose, T [1 ]
Nemoto, H [1 ]
机构
[1] Toyama Med & Pharmaceut Univ, Fac Pharmaceut Sci, Toyama 9300194, Japan
关键词
indium and compounds; fluorine and compounds;
D O I
10.1016/S0040-4020(00)00749-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Aldehydes reacted with 3-bromo-3,3-difluoropropene at the a-position in the presence of indium to afford 1-substituted-2,2-difluorobut-3-en-1-ols. Ketones and other electrophiles are inert under the examined conditions. The reaction of bromodifluoromethyl-acetylene derivatives with an aldehyde in the presence of indium provided difluorohomopropargylic alcohols. These reactions efficiently proceeded in polar solvents (water, DMF) under mild conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:8275 / 8280
页数:6
相关论文
共 28 条
[1]   INDIUM IN ORGANIC-SYNTHESIS - INDIUM-MEDIATED ALLYLATION OF CARBONYL-COMPOUNDS [J].
ARAKI, S ;
ITO, H ;
BUTSUGAN, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (08) :1831-1833
[2]   SYNTHESIS OF PHOSPHONATE ANALOGS OF 1,3-BISPHOSPHOGLYCERIC ACID AND THEIR BINDING TO YEAST PHOSPHOGLYCERATE KINASE [J].
BLACKBURN, GM ;
JAKEMAN, DL ;
IVORY, AJ ;
WILLIAMSON, MP .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1994, 4 (21) :2573-2578
[3]   MONOFLUORO-METHYLENEBISPHOSPHONIC AND DIFLUORO-METHYLENEBISPHOSPHONIC ACIDS - ISOPOLAR ANALOGS OF PYROPHOSPHORIC ACID [J].
BLACKBURN, GM ;
ENGLAND, DA ;
KOLKMANN, F .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (17) :930-932
[4]   THE SYNTHESIS AND METAL-BINDING CHARACTERISTICS OF NOVEL, ISOPOLAR PHOSPHONATE ANALOGS OF NUCLEOTIDES [J].
BLACKBURN, GM ;
KENT, DE ;
KOLKMANN, F .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (05) :1119-1125
[5]   NONHYDROLYZABLE PHOSPHOTYROSYL MIMETICS FOR THE PREPARATION OF PHOSPHATASE-RESISTANT SH2 DOMAIN INHIBITORS [J].
BURKE, TR ;
SMYTH, MS ;
OTAKA, A ;
NOMIZU, M ;
ROLLER, PP ;
WOLF, G ;
CASE, R ;
SHOELSON, SE .
BIOCHEMISTRY, 1994, 33 (21) :6490-6494
[6]   Regioselectivity patterns featured by formaldehyde in the electrophilic addition to gem-difluoro and gem-dichloroallyl systems. An ab initio theoretical study [J].
Canepa, C ;
Tonachini, G .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (20) :7066-7076
[7]   FLUORINE IN ENZYME CHEMISTRY .2. THE PREPARATION OF DIFLUOROMETHYLENEPHOSPHONATE ANALOGS OF GLYCOLYTIC PHOSPHATES - APPROACHING AN ISOSTERIC AND ISOELECTRONIC PHOSPHATE MIMIC [J].
CHAMBERS, RD ;
JAOUHARI, R ;
OHAGAN, D .
TETRAHEDRON, 1989, 45 (16) :5101-5108
[8]   Indium-mediated organometallic reactions in aqueous media: The nature of the allylindium intermediate [J].
Chan, TH ;
Yang, Y .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (13) :3228-3229
[9]  
CINTAS P, 1995, SYNLETT, P1087
[10]   FLUORIDE ION-CATALYZED GENERATION AND CARBONYL ADDITION OF ALPHA-HALO CARBANIONS DERIVED FROM ALPHA-HALO ORGANO-SILICON COMPOUNDS [J].
FUJITA, M ;
OBAYASHI, M ;
HIYAMA, T .
TETRAHEDRON, 1988, 44 (13) :4135-4145