Palladium-catalyzed ortho-C(sp2)-H bromination of benzaldehydes via a monodentate transient directing group strategy

被引:15
作者
Yong, Qiyun [1 ]
Sun, Bing [1 ]
Zhang, Fang-Lin [1 ]
机构
[1] Wuhan Univ Technol, Sch Chem Chem Engn & Life Sci, Wuhan 430070, Hubei, Peoples R China
基金
中国国家自然科学基金;
关键词
Palladium; Monodentate; Transient directing group; Benzaldehyde; SUZUKI-MIYAURA; COUPLING REACTIONS; HALOGENATION; FUNCTIONALIZATION; CHLORINATION; BROMPERIDOL; BROMHEXINE; AROMATICS; EFFICIENT;
D O I
10.1016/j.tetlet.2019.151263
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A facile and efficient monodentate transient directing group strategy was developed to enable the palladium-catalyzed ortho-C(sp(2))-H bromination of benzaldehydes. A broad scope of benzaldehydes were transformed into the desired products by employing 2-amino-5-chlorobenzotrifluoride as a monodentate transient directing group, demonstrating good functional group tolerance. Mild reaction conditions and no requirement for a silver salt are also features of this strategy. (C) 2019 Elsevier Ltd. All rights reserved.
引用
收藏
页数:4
相关论文
共 43 条
[1]  
Ali P., 2018, IND ENG CHEM RES, V57, P12314
[2]   Benzothiophene Carboxamide Derivatives as Inhibitors of Plasmodium falciparum Enoyl-ACP Reductase [J].
Banerjee, Tanushree ;
Sharma, Shailendra Kumar ;
Kapoor, Neha ;
Dwivedi, Vishnu ;
Surolia, Namita ;
Surolia, Avadhesha .
IUBMB LIFE, 2011, 63 (12) :1101-1110
[3]   RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION [J].
CABRI, W ;
CANDIANI, I .
ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) :2-7
[4]   Synthesis of a Novel Cellulose Microencapsulated Palladium Nanoparticle and Its Catalytic Activities in Suzuki-Miyaura and Mizoroki-Heck Reactions [J].
Chen, Feiran ;
Huang, Mingming ;
Li, Yiqun .
INDUSTRIAL & ENGINEERING CHEMISTRY RESEARCH, 2014, 53 (20) :8339-8345
[5]   Pd-Catalyzed, ortho C-H Methylation and Fluorination of Benzaldehydes Using Orthanilic Acids as Transient Directing Groups [J].
Chen, Xiao-Yang ;
Sorensen, Erik J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (08) :2789-2792
[6]   Pd-Catalyzed Ortho C-H Hydroxylation of Benzaldehydes Using a Transient Directing Group [J].
Chen, Xiao-Yang ;
Ozturk, Seyma ;
Sorensen, Erik J. .
ORGANIC LETTERS, 2017, 19 (23) :6280-6283
[7]   Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group [J].
Chen, Xiao-Yang ;
Ozturk, Seyma ;
Sorensen, Erik J. .
ORGANIC LETTERS, 2017, 19 (05) :1140-1143
[8]   Recent advances in Sonogashira reactions [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (10) :5084-5121
[9]   BROMPERIDOL, A NEW BUTYROPHENONE NEUROLEPTIC - A REVIEW [J].
DUBINSKY, B ;
MCGUIRE, JL ;
NIEMEGEERS, CJE ;
JANSSEN, PAJ ;
WEINTRAUB, HS ;
MCKENZIE, BE .
PSYCHOPHARMACOLOGY, 1982, 78 (01) :1-7
[10]   Sonogashira Couplings Catalyzed by Collaborative (N-Heterocyclic Carbene)-Copper and -Palladium Complexes [J].
Gallop, Christopher W. D. ;
Chen, Ming-Tsz ;
Navarro, Oscar .
ORGANIC LETTERS, 2014, 16 (14) :3724-3727