Transition-metal-catalyzed aldehydic C-H activation by azodicarboxylates

被引:49
作者
Lee, DS [1 ]
Otte, RD [1 ]
机构
[1] Univ Wisconsin, Dept Chem, Madison, WI 53706 USA
关键词
D O I
10.1021/jo035456o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Rhodium acetate-catalyzed hydroacylation between aldehydes and an activated form of N=N bond was achieved under mild conditions to provide efficient access to a variety of hydrazino imides. Good selectivity for the aldehydie C-H activation relative to the ene-type reaction was observed with aldehydes having unsaturation both at terminal and internal positions.
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收藏
页码:3569 / 3571
页数:3
相关论文
共 29 条
[1]   STUDIES ON DIMETHYLHYDRAZONES OF HETEROARYL ALDEHYDES - THE REACTIVITY OF 2-FORMYLFURAN, 2-FORMYLTHIOPHENE AND 1-METHYL-2-FORMYLPYRROLE N,N-DIMETHYLHYDRAZONES WITH METHYL PROPIOLATE AND DIETHYL AZODICARBOXYLATE [J].
ABARCA, B ;
BALLESTEROS, R ;
GONZALEZ, E ;
SANCHO, P ;
SEPULVEDA, J ;
SORIANO, C .
HETEROCYCLES, 1990, 31 (10) :1811-1817
[2]   ZUR REAKTION VON CYCLOHEXADIEN-(1.3) MIT AZODICARBONSAURE-DIATHYLESTER [J].
ASKANI, R .
CHEMISCHE BERICHTE-RECUEIL, 1965, 98 (08) :2551-&
[3]   ALLYLIC AMINATION BY THE LEWIS-ACID-MEDIATED ENE REACTION OF DIETHYL AZODICARBOXYLATE WITH ALKENES [J].
BRIMBLE, MA ;
HEATHCOCK, CH .
JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (19) :5261-5263
[4]   KINETIC AND SPECTROSCOPIC STUDIES ON ACYL RADICALS IN SOLUTION BY TIME-RESOLVED INFRARED-SPECTROSCOPY [J].
BROWN, CE ;
NEVILLE, AG ;
RAYNER, DM ;
INGOLD, KU ;
LUSZTYK, J .
AUSTRALIAN JOURNAL OF CHEMISTRY, 1995, 48 (02) :363-379
[5]  
Chatgilialoglu C, 1997, CHEM-EUR J, V3, P376
[6]   Chemistry of acyl radicals [J].
Chatgilialoglu, C ;
Crich, D ;
Komatsu, M ;
Ryu, I .
CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069
[7]   PHOTOCHEMICAL REACTION OF DIETHYL AZODICARBOXYLATE WITH ETHERS AND ALCOHOLS [J].
COOKSON, RC ;
STEVENS, IDR ;
WATTS, CT .
CHEMICAL COMMUNICATIONS, 1965, (12) :259-&
[8]   Radical-chain addition of aldehydes to alkenes catalysed by thiols [J].
Dang, HS ;
Roberts, BP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1998, (01) :67-75
[9]   Novel N-demethylation of ketolide:: application to the solution phase parallel synthesis of N-desosaminyl-substituted ketolides using ion exchange resins [J].
Denis, A ;
Renou, C .
TETRAHEDRON LETTERS, 2002, 43 (23) :4171-4174
[10]   SOLVENT EFFECT IN PERICYCLIC-REACTIONS .9. THE ENE REACTION [J].
DESIMONI, G ;
FAITA, G ;
RIGHETTI, PP ;
SFULCINI, A ;
TSYGANOV, D .
TETRAHEDRON, 1994, 50 (06) :1821-1832