Copper-catalyzed direct alkylation of heteroarenes

被引:81
作者
Theunissen, Cedric [1 ]
Wang, Jianjun [1 ]
Evano, Gwilherm [1 ]
机构
[1] Univ Libre Bruxelles, Lab Chim Organ, Serv Chim & Physicochim Organ, Ave FD Roosevelt 50,CP160-06, B-1050 Brussels, Belgium
关键词
C-H BOND; ELECTRON-RICH HETEROCYCLES; NITROGEN NUCLEOPHILES; RADICAL ALKYLATION; GOLD CATALYSIS; SECONDARY; HALIDES; BROMIDES; LIGAND; FUNCTIONALIZATION;
D O I
10.1039/c6sc05622a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient and broadly applicable process is reported for the direct alkylation of C-H bonds in heteroarenes, privileged scaffolds in many areas of science. This reaction is based on the copper-catalyzed addition of alkyl radicals generated from activated secondary and tertiary alkyl bromides to a wide range of arenes, including furans, thiophenes, pyrroles, and their benzo-fused derivatives, as well as coumarins and quinolinones.
引用
收藏
页码:3465 / 3470
页数:6
相关论文
共 64 条
[1]   User-Friendly [(Diglyme)NiBr2]-Catalyzed Direct Alkylations of Heteroarenes with Unactivated Alkyl Halides through C-H Bond Cleavages [J].
Ackermann, Lutz ;
Punji, Benudhar ;
Song, Weifeng .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (18) :3325-3329
[2]   Metal-catalyzed direct alkylations of (hetero)arenes via C-H bond cleavages with unactivated alkyl halides [J].
Ackermann, Lutz .
CHEMICAL COMMUNICATIONS, 2010, 46 (27) :4866-4877
[3]   Nickel-Catalyzed Direct Alkylation of C-H Bonds in Benzamides and Acrylamides with Functionalized Alkyl Halides via Bidentate-Chelation Assistance [J].
Aihara, Yoshinori ;
Chatani, Naoto .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (14) :5308-5311
[4]   Direct Selective Oxidative Cross-Coupling of Simple Alkanes with Heteroarenes [J].
Antonchick, Andrey P. ;
Burgmann, Lars .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) :3267-3271
[5]   Expedient Iron-Catalyzed C-H Allylation/ Alkylation by Triazole Assistance with Ample Scope [J].
Cera, Gianpiero ;
Haven, Tobias ;
Ackermann, Lutz .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (04) :1484-1488
[6]   Intramolecular 1,5-H transfer reaction of aryl iodides through visible-light photoredox catalysis: a concise method for the synthesis of natural product scaffolds [J].
Chen, Jian-Qiang ;
Wei, Yun-Long ;
Xu, Guo-Qiang ;
Liang, Yong-Min ;
Xu, Peng-Fei .
CHEMICAL COMMUNICATIONS, 2016, 52 (38) :6455-6458
[7]   Metalated heterocycles and their applications in synthetic organic chemistry [J].
Chinchilla, R ;
Nájera, C ;
Yus, M .
CHEMICAL REVIEWS, 2004, 104 (05) :2667-2722
[8]   Copper Catalyzed Atom Transfer Radical Cyclization Reactions [J].
Clark, Andrew J. .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 2016 (13) :2231-2243
[9]   Copper-catalyzed cyclization of iodo-tryptophans:: A straightforward synthesis of pyrroloindoles [J].
Coste, Alexis ;
Toumi, Mathieu ;
Wright, Karen ;
Razafimahaleo, Vanessa ;
Couty, Francois ;
Marrot, Jerome ;
Evano, Gwilherm .
ORGANIC LETTERS, 2008, 10 (17) :3841-3844
[10]   Synthesis of Ketene N,N-Acetals by Copper-Catalyzed Double-Amidation of 1,1-Dibromo-1-alkenes [J].
Coste, Alexis ;
Couty, Francois ;
Evano, Gwilherm .
ORGANIC LETTERS, 2009, 11 (19) :4454-4457