Palladium-catalyzed ortho-selective C-H bond chlorination of aromatic ketones

被引:9
作者
Shan, Gang [2 ,3 ]
Huang, Gui-Yi [1 ,2 ,3 ]
Rao, Yu [2 ,3 ]
Zhang, Hui [1 ]
机构
[1] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China
[2] Tsinghua Univ, Sch Med, Dept Pharmacol & Pharmaceut Sci, MOE Key Lab Prot Sci, Beijing 100084, Peoples R China
[3] Tsinghua Univ, Sch Life Sci, Beijing 100084, Peoples R China
关键词
Palladium catalysis; C-H chlorination; Aromatic ketones; ONE-POT SYNTHESIS; BIOLOGICAL-ACTIVITY; WEAK COORDINATION; HALOGENATION; ACYLATION; ARENES; REACTIVITY; EFFICIENT;
D O I
10.1016/j.cclet.2015.07.011
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A palladium-catalyzed ortho-selective C-H bond chlorination reaction for the preparation of 2-chloro aromatic ketones was described. Both electron-withdrawing and electron-donating groups on the aromatic rings are well tolerated under the optimized conditions. The 2-chloro aromatic ketones obtained by our method could be applied to synthesize the derivatives of 1H-indazole or benzo[d]isoxazole. (C) 2015 Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences. Published by Elsevier B.V. All rights reserved.
引用
收藏
页码:1236 / 1240
页数:5
相关论文
共 30 条
[1]   The influence of n-alkyl groups on the rate of a cyclization reaction [J].
Berliner, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1944, 66 :533-535
[2]  
BHAWAL B M, 1978, Marathwada University Journal of Sciences, V17, P21
[3]   Assembly of indole-2-carboxylic acid esters through a ligand-free copper-catalysed cascade process [J].
Cai, Qian ;
Li, Zhengqiu ;
Wei, Jiajia ;
Ha, Chengyong ;
Pei, Duanqing ;
Ding, Ke .
CHEMICAL COMMUNICATIONS, 2009, (48) :7581-7583
[4]   Rhodium(III)-catalyzed ortho-olefination of aryl phosphonates [J].
Chary, Bathoju Chandra ;
Kim, Sunggak .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2013, 11 (40) :6879-6882
[5]   A Versatile Protocol for the Preparation of Highly Hindered Aryl Ketones Using Organozinc Reagents [J].
Cho, Hyun-Hee ;
Kim, Seung-Hoi .
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2012, 33 (09) :3083-3086
[6]  
Engle KM., 2012, ACCOUNTS CHEM RES, V45, P788, DOI DOI 10.1021/ar200185g
[7]   Copper(I) Iodide Catalyzed Synthesis of Quinolinones via Cascade Reactions of 2-Halobenzocarbonyls with 2-Arylacetamides [J].
Fu, Liangbing ;
Huang, Xiaoli ;
Wang, Deping ;
Zhao, Pinghua ;
Ding, Ke .
SYNTHESIS-STUTTGART, 2011, (10) :1547-1554
[8]   Acylation of Grignard reagents mediated by N-methylpyrrolidone: A remarkable selectivity for the synthesis of ketones [J].
Gowda, Maravanhalli Sidde ;
Pande, Sushanth Sudhir ;
Ramakrishna, Ramesha Andagar ;
Prabhu, Kandikere Ramaiah .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (15) :5365-5368
[9]   Antimony(V) chloride-benzyltriethylammonium chloride complex as an efficient catalyst for Friedel-crafts acylation reactions [J].
Huang, AP ;
Liu, XY ;
Li, LH ;
Wu, XL ;
Liu, WM ;
Liang, YM .
ADVANCED SYNTHESIS & CATALYSIS, 2004, 346 (06) :599-602
[10]   Synthesis of 3-substituted indazoles and benzoisoxazoles via Pd-catalyzed cyclization reactions: application to the synthesis of nigellicine [J].
Inamoto, Kiyofumi ;
Katsuno, Mika ;
Yoshino, Takashi ;
Arai, Yukari ;
Hiroya, Kou ;
Sakamoto, Takao .
TETRAHEDRON, 2007, 63 (12) :2695-2711