Intermolecular radical carboaminohydroxylation of olefins with aryl diazonium salts and TEMPO

被引:100
作者
Heinrich, Markus R. [1 ]
Wetzel, Alexander [1 ]
Kirschstein, Marcel [1 ]
机构
[1] Tech Univ Munich, Lehrstuhl Organ Chem 1, D-85747 Garching, Germany
关键词
D O I
10.1021/ol701622d
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Highly reactive aryl radicals can selectively be reacted with a broad variety of activated and nonactivated olefinic substrates in the presence of nitroxyl radicals. Direct recombination of the aryl radical and the nitroxide as well as telomerization of the olefin is successfully suppressed by the reaction conditions.
引用
收藏
页码:3833 / 3835
页数:3
相关论文
共 44 条
[1]   REACTIONS OF ORTHO-ALKENYLOXYARENEDIAZONIUM FLUOROBORATES AND RELATED SPECIES WITH NITROXIDES [J].
BECKWITH, ALJ ;
MEIJS, GF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (12) :595-597
[2]   KINETICS OF NITROXIDE RADICAL TRAPPING .1. SOLVENT EFFECTS [J].
BECKWITH, ALJ ;
BOWRY, VW ;
INGOLD, KU .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (13) :4983-4992
[3]   Carbodiazenylation of olefins by radical iodine transfer and addition to arenediazonium salts [J].
Blank, Olga ;
Heinrich, Markus R. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2006, 2006 (19) :4331-4334
[4]   AN EFFICIENT SYNTHESIS OF 1,2,9,9A-TETRAHYDROCYCLOPROPA[C]BENZ[E]INDOL-4-ONE (CBI) - AN ENHANCED AND SIMPLIFIED ANALOG OF THE CC-1065 AND DUOCARMYCIN ALKYLATION SUBUNITS [J].
BOGER, DL ;
MCKIE, JA .
JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (05) :1271-1275
[5]   One-pot four-component reaction:: Aqueous TiCl3/PhN2+-mediated alkyl radical addition to imines generated in situ [J].
Cannella, R ;
Clerici, A ;
Pastori, N ;
Regolini, E ;
Porta, O .
ORGANIC LETTERS, 2005, 7 (04) :645-648
[6]   FREE-RADICAL DIAZO COUPLING - A NEW GENERAL REACTION OF DIAZONIUM SALTS [J].
CITTERIO, A ;
MINISCI, F .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (09) :1759-1761
[7]   STERIC, POLAR, AND RESONANCE EFFECTS IN REACTIVITY AND REGIOSELECTIVITY OF ARYL RADICAL-ADDITION TO ALPHA,BETA-UNSATURATED CARBONYL-COMPOUNDS [J].
CITTERIO, A ;
MINISCI, F ;
VISMARA, E .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (01) :81-88
[8]   TiCl3/PhN2+-mediated radical addition of ethers to aldimines generated in situ under aqueous conditions [J].
Clerici, A ;
Cannella, R ;
Panzeri, W ;
Pastori, N ;
Regolini, E ;
Porta, O .
TETRAHEDRON LETTERS, 2005, 46 (48) :8351-8354
[9]   ARYLATIVE AMINATION OF ALDEHYDES PROMOTED BY AQUEOUS TITANIUM TRICHLORIDE [J].
CLERICI, A ;
PORTA, O .
TETRAHEDRON LETTERS, 1990, 31 (14) :2069-2072
[10]   A free radical Mannich type reaction:: selective α-CH aminomethylation of ethers by Ti(III)/t-BuOOH system under aqueous acidic conditions [J].
Clerici, Angelo ;
Cannella, Rosalba ;
Pastori, Nadia ;
Panzeri, Walter ;
Porta, Ombretta .
TETRAHEDRON, 2006, 62 (25) :5986-5994