Efficient conversion of ketones to α-tosyloxyketones with m-chloroperbenzoic acid and p-toluenesulfonic acid in the presence of catalytic amount of IL-Supported phl in [emim]OTs

被引：56
作者：
Akiike, Junnosuke [1 ]
Yamamoto, Yukiharu [1 ]
Togo, Hideo [1 ]
机构：
[1] Chiba Univ, Grad Sch Sci, Inage Ku, Chiba 263, Japan
来源：
SYNLETT | 2007年 / 14期
关键词：
ionic liquid; IL-supported Phl; alpha-tosytoxyketone; ketone; MCPBA; p-toluenesulfonic acid; thiazole; catalyst;
D O I：
10.1055/s-2007-984914
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Various ketones were smoothly converted into the corresponding alpha-tosyloxyketones with MCPBA and p-toluenesulfonic acid in the presence of a catalytic amount of ionic-liquid (IL)-supported PhI in room temperature ionic liquid, [emim]OTs. Moreover, the present ionic-liquid reaction media containing a catalytic amount of IL-supported PhI could be reused for the same alpha-tosyloxylation of ketones and thiazoles directly, keeping good yields.
引用
收藏
页码：2168 / 2172
页数：5
相关论文
共 103 条
[1]  
Abe S, 2001, SYNLETT, P22
[2]   Synthetic use of poly[4-hydroxy(tosyloxy)iodo]styrenes [J].
Abe, S ;
Sakuratani, K ;
Togo, H .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (18) :6174-6177
[3]   Stereoselective hydrogenation reactions in chloroaluminate(III) ionic liquids: a new method for the reduction of aromatic compounds [J].
Adams, CJ ;
Earle, MJ ;
Seddon, KR .
CHEMICAL COMMUNICATIONS, 1999, (11) :1043-1044
[4]  
Adams CJ, 1998, CHEM COMMUN, P2097
[5]   Molecular sieves in ionic liquids as an efficient and recyclable medium for the synthesis of imines [J].
Andrade, CKZ ;
Takada, SCS ;
Alves, LM ;
Rodrigues, JP ;
Suarez, PAZ ;
Brandao, RF ;
Soares, VCD .
SYNLETT, 2004, (12) :2135-2138
[6]   TEMPO-catalyzed aerobic oxidation of alcohols to aldehydes and ketones in ionic liquid [bmim][PF6] [J].
Ansari, IA ;
Gree, R .
ORGANIC LETTERS, 2002, 4 (09) :1507-1509
[7]   QUATERNIZATION OF THIAZOLES [J].
BEHERA, GB ;
KAR, JN ;
ACHARYA, RC ;
ROUT, MK .
JOURNAL OF ORGANIC CHEMISTRY, 1973, 38 (12) :2164-2166
[8]   Ionic liquids as reaction media for esterification of carboxylate sodium salts with alkyl halides [J].
Brinchi, L ;
Germani, R ;
Savelli, G .
TETRAHEDRON LETTERS, 2003, 44 (10) :2027-2029
[9]   Efficient esteritication of carboxylic acids with alkyl halides catalyzed by fluoride ions in ionic liquids [J].
Brinchi, L ;
Germani, R ;
Savelli, G .
TETRAHEDRON LETTERS, 2003, 44 (35) :6583-6585
[10]   Heck reaction in ionic liquids catalyzed by a Pd-benzothiazole carbene complex [J].
Calò, V ;
Nacci, A ;
Lopez, L ;
Mannarini, N .
TETRAHEDRON LETTERS, 2000, 41 (46) :8973-8976
12345678910