Continuous flow palladium-catalyzed trifluoromethylthiolation of C-H bonds

被引:13
作者
Bouchard, Alexanne [1 ,2 ]
Kairouz, Vanessa [1 ,2 ]
Manneveau, Maxime [3 ]
Xiong, Heng-Ying [3 ]
Besset, Tatiana [3 ]
Pannecoucke, Xavier [3 ]
Lebel, Helene [1 ,2 ]
机构
[1] Univ Montreal, Dept Chem, POB 6128, Montreal, PQ, Canada
[2] Univ Montreal, Continuous Flow Synth Lab, POB 6128, Montreal, PQ, Canada
[3] Normandie Univ, INSA Rouen, CNRS, UNIROUEN,COBRA,UMR 6014, F-76000 Rouen, France
基金
加拿大创新基金会; 加拿大自然科学与工程研究理事会;
关键词
Aminoquinoline; Bidentate directing group; C-SCF3; bond; Organofluorine compounds; Flow process; C-H activation; Halogenation; Trifluoromethylthioethers; FUNCTIONALIZATION; ACTIVATION;
D O I
10.1007/s41981-018-0023-4
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A continuous flow process for the synthesis of trifluoromethylthioethers is reported. The palladium-catalyzed C-H trifluoromethylthiolation of amides derived from the 8-aminoquinoline using N-[(trifluoromethyl)thio]phthalimide produced the desired products in moderate to good yields with a residence time of 20 min. In comparison with the batch process, the reaction time was decreased by a factor of 100 to 200, demonstrating the positive effect of continuous flow processes for this type of reaction.
引用
收藏
页码:9 / 12
页数:4
相关论文
共 31 条
[1]   Late stage trifluoromethylthiolation strategies for organic compounds [J].
Barata-Vallejo, Sebastian ;
Bonesi, Sergio ;
Postigo, Al .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (30) :7150-7182
[2]   State-of-the-Art in Electrophilic Trifluoromethylthiolation Reagents [J].
Chachignon, Helene ;
Cahard, Dominique .
CHINESE JOURNAL OF CHEMISTRY, 2016, 34 (05) :445-454
[3]   Copper-Catalyzed Direct Trifluoromethylthiolation of Benzylic C-H Bonds via Nondirected Oxidative C(sp3)-H Activation [J].
Chen, Chao ;
Xu, Xiu-Hua ;
Yang, Bin ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2014, 16 (12) :3372-3375
[4]   8-Aminoquinoline: A Powerful Directing Group in Metal-Catalyzed Direct Functionalization of C-H Bonds [J].
Corbet, Matthieu ;
De Campo, Floryan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (38) :9896-9898
[5]   Silver-Mediated Oxidative Aliphatic C-H Trifluoromethylthiolation [J].
Guo, Shuo ;
Zhang, Xiaofei ;
Tang, Pingping .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (13) :4065-4069
[6]   Forbidden Chemistries - Paths to a Sustainable Future Engaging Continuous Processing [J].
Gutmann, Bernhard ;
Kappe, C. Oliver .
JOURNAL OF FLOW CHEMISTRY, 2017, 7 (3-4) :65-71
[7]   A SURVEY OF HAMMETT SUBSTITUENT CONSTANTS AND RESONANCE AND FIELD PARAMETERS [J].
HANSCH, C ;
LEO, A ;
TAFT, RW .
CHEMICAL REVIEWS, 1991, 91 (02) :165-195
[8]   Palladium-Catalyzed Trifluoromethylthiolation of Chelation-Assisted C-H Bonds [J].
Kesavan, Arunachalam ;
Chaitanya, Manthena ;
Anbarasan, Pazhamalai .
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (25) :3276-3279
[9]   Fluorine and Fluorinated Motifs in the Design and Application of Bioisosteres for Drug Design [J].
Meanwell, Nicholas A. .
JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (14) :5822-5880
[10]   Enhanced Reaction Efficiency in Continuous Flow [J].
Morse, Peter D. ;
Beingessner, Rachel L. ;
Jamison, Timothy F. .
ISRAEL JOURNAL OF CHEMISTRY, 2017, 57 (3-4) :218-227