Formation of 1,2-diketones by samarium diiodide promoted reaction of N-acylbenzotriazoles

被引:25
作者
Wang, XX
Zhang, YM
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310028, Peoples R China
[2] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
samarium diiodide; reductive coupling; acylbenzotriazoles; 1,2-diketones; vic-dibenzotriazoylalkene;
D O I
10.1016/S0040-4039(02)01080-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Transformation of N-acylbenzotriazoles 1 into 1,2-diketones 2 in good to excellent yields has been realized by the use of samarium diiodide at room temperature. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:5431 / 5433
页数:3
相关论文
共 17 条
[1]   CYCLIZATION REACTIONS OF ALPHA-AMINO RADICALS DERIVED FROM N-(N',N'-DIALKYLAMINOALKENYL)BENZOTRIAZOLES AND SAMARIUM DIIODIDE [J].
AURRECOECHEA, JM ;
FERNANDEZACEBES, A .
TETRAHEDRON LETTERS, 1993, 34 (03) :549-552
[2]   Sm or Zn-induced coupling reactions. A facile route to 1,2-diketones [J].
Baruah, B ;
Boruah, A ;
Prajapati, D ;
Sandhu, JS .
TETRAHEDRON LETTERS, 1997, 38 (43) :7603-7604
[3]   ORGANOMETALLIC COMPOUNDS OF BIVALENT EUROPIUM, YTTERBIUM, AND SAMARIUM [J].
EVANS, DF ;
FAZAKERLEY, GV ;
PHILLIPS, RF .
JOURNAL OF THE CHEMICAL SOCIETY A -INORGANIC PHYSICAL THEORETICAL, 1971, (11) :1931-+
[4]   AN EASY COUPLING OF ACID-CHLORIDES INTO ALPHA-DIKETONES PROMOTED BY DIIODOSAMARIUM [J].
GIRARD, P ;
COUFFIGNAL, R ;
KAGAN, HB .
TETRAHEDRON LETTERS, 1981, 22 (40) :3959-3960
[5]   BENZOTRIAZOLE-MEDIATED ARYLALKYLATION AND HETEROARYLALKYLATION [J].
KATRITZKY, AR ;
LAN, XF .
CHEMICAL SOCIETY REVIEWS, 1994, 23 (06) :363-373
[6]  
KATRITZKY AR, 1994, SYNTHESIS-STUTTGART, P445
[7]   N-acylbenzotriazoles:: Neutral acylating reagents for the preparation of primary, secondary, and tertiary amides [J].
Katritzky, AR ;
He, HY ;
Suzuki, K .
JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (24) :8210-8213
[8]   Properties and synthetic utility of N-substituted benzotriazoles [J].
Katritzky, AR ;
Lan, XF ;
Yang, JZ ;
Denisko, OV .
CHEMICAL REVIEWS, 1998, 98 (02) :409-548
[9]   BENZOTRIAZOLE - A NOVEL SYNTHETIC AUXILIARY [J].
KATRITZKY, AR ;
RACHWAL, S ;
HITCHINGS, GJ .
TETRAHEDRON, 1991, 47 (16-17) :2683-2732
[10]  
KATRITZKY AR, 1994, ALDRICHIM ACTA, V27, P31