Copper-catalyzed, ceric ammonium nitrate mediated N-arylation of amines

被引：0
作者：
Gonela, Uma Maheshwar [1 ]
Ablordeppey, Seth Y. [1 ]
机构：
[1] Florida A&M Univ, Coll Pharm & Pharmaceut Sci, Div Basic Pharmaceut Sci, Tallahassee, FL 32307 USA
来源：
NEW JOURNAL OF CHEMISTRY | 2019年 / 43卷 / 07期
关键词：
CROSS-COUPLING REACTIONS; HETEROATOM BOND FORMATION; ARYLBORONIC ACIDS; C-N; BORONIC ACIDS; ARYL HALIDES; PHENYLBORONIC ACIDS; CARBON-CARBON; ROOM-TEMPERATURE; SODIUM-NITRITE;
D O I：
10.1039/c8nj06145a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Cu-Catalyzed, ligand- and base-free cross-coupling of aryl boronic acids with primary and secondary amines has been reported. This 'Chan-Evans-Lam' reaction has revealed that at room temperature, with a catalytic amount of copper(II) acetate and ceric ammonium nitrate (CAN) as an oxidant, N-arylation can result in an effective C-N bond formation. This air stable, practical, robust protocol enables tolerance towards a variety of functional groups on both boronic acid and amine partners.
引用
收藏
页码：2861 / 2864
页数：4
相关论文
共 87 条
[1]   Identification of a butyrophenone analog as a potential atypical antipsychotic agent: 4-[4-(4-Chlorophenyl)-1,4-diazepan-1-yl]-1(4-fluorophenyl)butan-1-one [J].
Ablordeppey, Seth Y. ;
Altundas, Ramazan ;
Bricker, Barbara ;
Zhu, Xue Y. ;
Kumar, Eyunni V. K. Suresh ;
Jackson, Tanise ;
Khan, Abdul ;
Roth, Bryan L. .
BIOORGANIC & MEDICINAL CHEMISTRY, 2008, 16 (15) :7291-U3
[2]  
[Anonymous], NAME REACTION
[3]   Copper-catalyzed coupling of arylboronic acids and amines [J].
Antilla, JC ;
Buchwald, SL .
ORGANIC LETTERS, 2001, 3 (13) :2077-2079
[4]   A mild and efficient new synthesis of aryl sulfones from boronic acids and sulfinic acid salts [J].
Beaulieu, C ;
Guay, D ;
Wang, ZY ;
Evans, DA .
TETRAHEDRON LETTERS, 2004, 45 (16) :3233-3236
[5]   C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents [J].
Beccalli, Egle M. ;
Broggini, Gianluigi ;
Martinelli, Michela ;
Sottocornola, Silvia .
CHEMICAL REVIEWS, 2007, 107 (11) :5318-5365
[6]   Transition-metal-catalyzed reactions of carbon-heteroatom bond formation by substitution and addition processes [J].
Beletskaya, IP .
PURE AND APPLIED CHEMISTRY, 2005, 77 (12) :2021-2027
[7]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[8]  
Buchwald SL, 2008, ACCOUNTS CHEM RES, V41, P1439, DOI 10.1021/ar8001798
[9]   New N- and O-arylations with phenylboronic acids and cupric acetate [J].
Chan, DMT ;
Monaco, KL ;
Wang, RP ;
Winters, MP .
TETRAHEDRON LETTERS, 1998, 39 (19) :2933-2936
[10]   An efficient diamine copper complex-catalyzed coupling of arylboronic acids with imidazoles [J].
Collman, JP ;
Zhong, M .
ORGANIC LETTERS, 2000, 2 (09) :1233-1236
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