Exceptionally Mild Palladium(II)-Catalyzed Dehydrogenative C-H/C-H Arylation of Indolines at the C-7 Position under Air

被引：77
作者：
Jiao, Lin-Yu [1 ]
Smirnov, Polina [1 ]
Oestreich, Martin [1 ]
机构：
[1] Tech Univ Berlin, Inst Chem, D-10623 Berlin, Germany
来源：
ORGANIC LETTERS | 2014年 / 16卷 / 22期
关键词：
CATALYZED ORTHO-ARYLATION; SIMPLE ARENES; BOND ACTIVATION; PALLADIUM CATALYSIS; OXIDATIVE ARYLATION; DIRECT OLEFINATION; FUNCTIONALIZATION; INDOLES; RHODIUM; POLYFLUOROARENES;
D O I：
10.1021/ol503035z
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An improved method for the dehydrogenative C-H/C-H cross-coupling at the C-7 position of indolines containing a urea as a directing group is reported. The new protocol is a rare example of an aerobic palladium(II)-catalyzed cross dehydrogenative coupling (CDC) reaction that proceeds at low temperature. The use of either Cu(OAc)(2) in an open flask or dioxygen (balloon) at 50 degrees C tolerates indolines not substituted at C-2 and C-3, thereby extending the scope of the previous method that suffers from indoline-to-indole oxidation.
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收藏
页码：6020 / 6023
页数：4
相关论文
共 65 条
[1]   Transition-Metal-Catalyzed Direct Arylation of (Hetero)Arenes by C-H Bond Cleavage [J].
Ackermann, Lutz ;
Vicente, Ruben ;
Kapdi, Anant R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (52) :9792-9826
[2]   Rhodium(III)- and Iridium(III)-Catalyzed C7 Alkylation of Indolines with Diazo Compounds [J].
Ai, Wen ;
Yang, Xueyan ;
Wu, Yunxiang ;
Wang, Xuan ;
Li, Yuanchao ;
Yang, Yaxi ;
Zhou, Bing .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (52) :17653-17657
[3]   Twofold C-H functionalization:: Palladium-catalyzed ortho arylation of anilides [J].
Brasche, Gordon ;
Garcia-Fortanet, Jorge ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2008, 10 (11) :2207-2210
[4]   Regiocontrolled aerobic oxidative coupling of indoles and benzene using Pd catalysts with 4,5-diazafluorene ligands [J].
Campbell, Alison N. ;
Meyer, Eric B. ;
Stahl, Shannon S. .
CHEMICAL COMMUNICATIONS, 2011, 47 (37) :10257-10259
[5]   Recent advances in the transition metal-catalyzed twofold oxidative C-H bond activation strategy for C-C and C-N bond formation [J].
Cho, Seung Hwan ;
Kim, Ji Young ;
Kwak, Jaesung ;
Chang, Sukbok .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5068-5083
[6]   Rhodium or Ruthenium-Catalyzed Oxidative C?H/C?H Cross-Coupling: Direct Access to Extended p-Conjugated Systems [J].
Dong, Jiaxing ;
Long, Zhen ;
Song, Feijie ;
Wu, Ningjie ;
Guo, Qiang ;
Lan, Jingbo ;
You, Jingsong .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (02) :580-584
[7]   Palladium(II)-Catalyzed Oxidative C-H/C-H Cross-Coupling between Two Structurally Similar Azoles [J].
Dong, Jiaxing ;
Huang, Yumin ;
Qin, Xurong ;
Cheng, Yangyang ;
Hao, Jing ;
Wan, Danyang ;
Li, Wei ;
Liu, Xingyan ;
You, Jingsong .
CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (20) :6158-6162
[8]   C-C bond formation via double C-H functionalization: Aerobic oxidative coupling as a method for synthesizing heterocoupled biaryls [J].
Dwight, Timothy A. ;
Rue, Nicholas R. ;
Charyk, Dagmara ;
Josselyn, Ryan ;
DeBoef, Brenton .
ORGANIC LETTERS, 2007, 9 (16) :3137-3139
[9]   Dual C-H activations of electron-deficient heteroarenes: palladium-catalyzed oxidative cross coupling of thiazoles with azine N-oxides [J].
Fu, Xiao-Pu ;
Xuan, Qing-Qing ;
Liu, Li ;
Wang, Dong ;
Chen, Yong-Jun ;
Li, Chao-Jun .
TETRAHEDRON, 2013, 69 (22) :4436-4444
[10]   Pd-catalyzed double C-H bond activation of diaryl ketones for the synthesis of fluorenones [J].
Gandeepan, Parthasarathy ;
Hung, Chen-Hsun ;
Cheng, Chien-Hong .
CHEMICAL COMMUNICATIONS, 2012, 48 (75) :9379-9381
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