Solvent-Free, Base-Free Microwave-Mediated Iridium-Catalyzed N-Alkylation of Amides with Alcohols

被引:13
作者
Apsunde, Tushar D. [1 ]
Trudell, Mark L. [1 ]
机构
[1] Univ New Orleans, Dept Chem, New Orleans, LA 70148 USA
来源
SYNTHESIS-STUTTGART | 2014年 / 46卷 / 02期
关键词
alcohol; alkylation; amide; iridium; BOND FORMATION; AMINES;
D O I
10.1055/s-0033-1340142
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Solvent-free, base-free microwave-mediated (Cp*IrCl2)(2)-catalyzed conditions for the N-alkylation of amides with alcohols have been developed. A series of primary and secondary alcohols have been shown to produce high yields of N-alkyl arylamides and N-alkyl alkylamides.
引用
收藏
页码:230 / 234
页数:5
相关论文
共 34 条
[1]   SOLVENT-FREE C-BENZOYLATION AND N-BENZOYLATION REACTIONS USING MICROWAVE HEATING [J].
Al-Masum, Mohammad ;
Wai, Maya Chen ;
Dunnenberger, Henry .
SYNTHETIC COMMUNICATIONS, 2011, 41 (19) :2888-2898
[2]   Uncatalyzed conversion of linear α-nitro ketones into amides by reaction with primary amines under solventless conditions [J].
Ballini, R ;
Bosica, G ;
Fiorini, D .
TETRAHEDRON, 2003, 59 (08) :1143-1145
[3]   o-Benzenedisulfonimide as a Reusable Bronsted Acid Catalyst for Ritter-Type Reactions [J].
Barbero, Margherita ;
Bazzi, Stefano ;
Cadamuro, Silvano ;
Dughera, Stefano .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (03) :430-436
[4]   N-benzylbenzamides: A new class of potent tyrosinase inhibitors [J].
Cho, SJ ;
Roh, JS ;
Sun, WS ;
Kim, SH ;
Park, KD .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (10) :2682-2684
[5]   Dehydrogenation as a Substrate-Activating Strategy in Homogeneous Transition-Metal Catalysis [J].
Dobereiner, Graham E. ;
Crabtree, Robert H. .
CHEMICAL REVIEWS, 2010, 110 (02) :681-703
[6]   N-Alkylation of amines with alcohols catalyzed by a Cp*Ir complex [J].
Fujita, K ;
Li, ZZ ;
Ozeki, N ;
Yamaguchi, R .
TETRAHEDRON LETTERS, 2003, 44 (13) :2687-2690
[7]   Cp*Ir-catalyzed N-alkylation of amines with alcohols. A versatile and atom economical method for the synthesis of amines [J].
Fujita, Ken-ichi ;
Enoki, Youichiro ;
Yamaguchi, Ryohei .
TETRAHEDRON, 2008, 64 (08) :1943-1954
[8]   N-Alkylation of carbamates and amides with alcohols catalyzed by a Cp*Ir complex [J].
Fujita, Ken-ichi ;
Komatsubara, Atsuo ;
Yamaguchi, Ryohei .
TETRAHEDRON, 2009, 65 (18) :3624-3628
[9]  
Greene T. W., 2007, GREENES PROTECTIVE G
[10]   Alcohols as electrophiles in C-C bond-forming reactions:: The hydrogen autotransfer process [J].
Guillena, Gabriela ;
Ramon, Diego J. ;
Yus, Miguel .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (14) :2358-2364