4-Substituted tert-Butyl Phenylazocarboxylates-Synthetic Equivalents for the para-Phenyl Radical Cation

被引:33
作者
Hoefling, Sarah B. [1 ]
Bartuschat, Amelie L. [1 ]
Heinrich, Markus R. [1 ]
机构
[1] Univ Erlangen Nurnberg, D-91052 Erlangen, Germany
关键词
arenes; aromatic substitution; nucleophilic substitution; radical reactions; synthetic methods; NUCLEOPHILIC AROMATIC-SUBSTITUTION; FRAGMENTIERUNG VON AZOVERBINDUNGEN; SECONDARY-AMINES; DISPLACEMENT; PHENYLDIIMIDE; NITROBENZENES; TAUTOMERISM; HETEROLYSIS; CHEMISTRY; ARYLATION;
D O I
10.1002/anie.201004508
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
First electrophile, then radical: 4-Substituted tert-butyl phenylazocarboxylates 1 are versatile synthetic equivalents of the para-phenyl radical cation 2. The tert-butyloxycarbonylazo group enables nucleophilic substitutions to proceed under mild conditions and can later be employed for the generation of aryl radicals. Copyright © 2010 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:9769 / 9772
页数:4
相关论文
共 71 条
[1]  
Ackermann L, 2009, MODERN ARYLATION METHODS, P1
[2]   DISPLACEMENT OF NITRITE ION IN NITROBENZENES BY SODIUM THIOLATES [J].
BAUMANN, JB .
JOURNAL OF ORGANIC CHEMISTRY, 1971, 36 (03) :396-&
[3]   Direct One-Step18F-Labeling of Peptides via Nucleophilic Aromatic Substitution [J].
Becaud, Jessica ;
Mu, Linjing ;
Karramkam, Mylene ;
Schubiger, Pius A. ;
Ametamey, Simon M. ;
Graham, Keith ;
Stellfeld, Timo ;
Lehmann, Lutz ;
Borkowski, Sandra ;
Berndorff, Dietmar ;
Dinkelborg, Ludger ;
Srinivasan, Ananth ;
Smits, Rene ;
Koksch, Beate .
BIOCONJUGATE CHEMISTRY, 2009, 20 (12) :2254-2261
[4]   NUCLEOPHILIC DISPLACEMENT OF AROMATIC NITRO-GROUPS [J].
BECK, JR .
TETRAHEDRON, 1978, 34 (14) :2057-2068
[5]   1.3-DIPOLAR CYCLOADDITIONS .69. REACTIONS OF AROMATIC NITRILE OXIDES WITH AZODICARBOXYLIC ESTER AND RELATED COMPOUNDS [J].
BLASCHKE, H ;
BRUNN, E ;
HUISGEN, R ;
MACK, W .
CHEMISCHE BERICHTE-RECUEIL, 1972, 105 (09) :2841-&
[6]  
Bowman WR, 1996, TETRAHEDRON, V52, P3961
[7]   Nucleophilicities of primary and secondary amines in water [J].
Brotzel, Frank ;
Chu, Ying Cheung ;
Mayr, Herbert .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (10) :3679-3688
[8]   PHOTOINDUCED ELECTRON-TRANSFER REACTION OF ARYL PERFLUOROALKANESULFONATES WITH ANILINES [J].
CHEN, QY ;
LI, ZT .
JOURNAL OF FLUORINE CHEMISTRY, 1994, 66 (01) :59-62
[9]   FORMATION OF PHENYLDIIMIDE AND PHENYL RADICAL BY HETEROLYSIS OF N-PHENYL-N]-BENZOYLDIIMIDE [J].
COHEN, SG ;
NICHOLSO.J .
JOURNAL OF ORGANIC CHEMISTRY, 1965, 30 (04) :1162-&
[10]   FORMATION OF PHENYL RADICAL BY HETEROLYSIS OF N-PHENYL-N]-BENZOYLDIIMIDE [J].
COHEN, SG ;
NICHOLSON, J .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1964, 86 (18) :3892-&