Sequential Direct SNAr Reactions of Pentafluorobenzenes with Azole or Indole Derivatives

被引:33
作者
Diness, Frederik [1 ]
Begtrup, Mikael [1 ]
机构
[1] Univ Copenhagen, Dept Drug Design & Pharmacol, DK-2100 Copenhagen, Denmark
关键词
ARYLATION; SUBSTITUTION; FLUORINE;
D O I
10.1021/ol5012554
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Sequential regioselective N-arylations through high-yielding catalyst-free direct SNAr reactions of pentafluor-obenzene derivatives with azole or indole derivatives are described. The N-arylated derivatives were further functionalized through a microwave-assisted cross-coupling reaction via C-H bond activation or Suzuki conditions. The order of the reactions could be reversed, proving full orthogonality between the reactions which led to well-defined fully substituted benzene derivatives.
引用
收藏
页码:3130 / 3133
页数:4
相关论文
共 28 条
[21]   Pillar height dependent formation of unprecedented Pd8 molecular swing and Pd6 molecular boat via multicomponent self-assembly [J].
Samanta, Dipak ;
Shanmugaraju, Sankarasekaran ;
Joshi, Sachin A. ;
Patil, Yogesh P. ;
Nethaji, Munirathinam ;
Mukherjee, Partha Sarathi .
CHEMICAL COMMUNICATIONS, 2012, 48 (17) :2298-2300
[22]   Pyrrole-Fused Azacoronene Family: The Influence of Replacement with Dialkoxybenzenes on the Optical and Electronic Properties in Neutral and Oxidized States [J].
Takase, Masayoshi ;
Narita, Tomoyuld ;
Fujita, Wataru ;
Asano, Motoko S. ;
Nishinaga, Tohru ;
Benten, Hiroaki ;
Yoza, Kenji ;
Muellen, Klaus .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (21) :8031-8040
[23]   Star-Shaped Pyrrole-Fused Tetrathiafulvalene Oligomers: Synthesis and Redox, Self-Assembling, and Conductive Properties [J].
Takase, Masayoshi ;
Yoshida, Naofumi ;
Nishinaga, Tohru ;
Iyoda, Masahiko .
ORGANIC LETTERS, 2011, 13 (15) :3896-3899
[24]   Organic host materials for phosphorescent organic light-emitting diodes [J].
Tao, Youtian ;
Yang, Chuluo ;
Qin, Jingui .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (05) :2943-2970
[25]   Highly efficient organic light-emitting diodes from delayed fluorescence [J].
Uoyama, Hiroki ;
Goushi, Kenichi ;
Shizu, Katsuyuki ;
Nomura, Hiroko ;
Adachi, Chihaya .
NATURE, 2012, 492 (7428) :234-+
[26]   Semiconducting π-Conjugated Systems in Field-Effect Transistors: A Material Odyssey of Organic Electronics [J].
Wang, Chengliang ;
Dong, Huanli ;
Hu, Wenping ;
Liu, Yunqi ;
Zhu, Daoben .
CHEMICAL REVIEWS, 2012, 112 (04) :2208-2267
[27]   Recent Progresses on Materials for Electrophosphorescent Organic Light-Emitting Devices [J].
Xiao, Lixin ;
Chen, Zhijian ;
Qu, Bo ;
Luo, Jiaxiu ;
Kong, Sheng ;
Gong, Qihuang ;
Kido, Junji .
ADVANCED MATERIALS, 2011, 23 (08) :926-952
[28]   Solvent controlled regioselective reaction of 1,2,3-benzotriazole (BtH) with pentafluorobenzene derivatives [J].
Zhao, Jingwei ;
Song, Tao ;
Zhu, Shizheng ;
Xu, Liangzhong .
TETRAHEDRON, 2011, 67 (05) :910-914