Copper-catalyzed bifunctionalization of alkenes with anilines and HFIP: Efficient access to 1,3-amino alcohols

被引:4
作者
Zhu, Fengxiang [1 ]
Deng, Peng [1 ]
Zhang, Pengbo [2 ]
机构
[1] Shanxi Univ, Sch Chem & Chem Engn, Wucheng Rd 92, Taiyuan 030006, Peoples R China
[2] Xinxiang Med Univ, Sch Publ Hlth, Xinxiang 453003, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper; Bifunctionalization; Alkenes; C-H activation; 3-amino alcohols; C-H AMINATION; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC HYDROGENATION; DIASTEREOSELECTIVE SYNTHESIS; BETA-KETOENAMIDES; FUNCTIONALIZATION; KETONES; BONDS; CARBON; 1,3-OXAZINANES;
D O I
10.1016/j.jcat.2024.115292
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
An interesting copper-catalyzed bifunctionalization of alkenes with anilines and HFIP has been achieved. Using readily available starting materials, a series of valuable complex highly functionalized 1,3-amino alcohols were isolated with moderate to good yields. Additionally, this protocol also presented a general and effective one-step procedure for the synthesis of 1,3-amino alcohols in an intermolecular manner.
引用
收藏
页数:6
相关论文
共 70 条
[61]   Preparation of Chiral γ-Secondary Amino Alcohols via Ni-Catalyzed Asymmetric Reductive Coupling of 2-Aza-butadiene with Aldehydes [J].
Yang, Lei ;
Shang, Weidong ;
Zhang, Li ;
Zhang, Xia .
ORGANIC LETTERS, 2022, 24 (42) :7763-7768
[62]   Iron-Catalyzed Intermolecular 1,2-Difunctionalization of Styrenes and Conjugated Alkenes with Silanes and Nucleophiles [J].
Yang, Yuan ;
Song, Ren-Jie ;
Ouyang, Xuan-Hui ;
Wang, Cheng-Yong ;
Li, Jin-Heng ;
Luo, Shenglian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) :7916-7919
[63]   Ru-Catalyzed Rearrangement of N-Methyl Isoxazolidines to N-H 1,3-Oxazinanes: A Strategy of Self-Hydride Transferring Cleavage of N-O Bonds [J].
Yao, Chuan-Zhi ;
Xiao, Zu-Feng ;
Liu, Jie ;
Ning, Xiao-Shan ;
Kang, Yan-Biao .
ORGANIC LETTERS, 2014, 16 (09) :2498-2501
[64]   Three-component Oxytrifluoromethylation of Alkenes: Highly Efficient and Regioselective Difunctionalization of C=C Bonds Mediated by Photoredox Catalysts [J].
Yasu, Yusuke ;
Koike, Takashi ;
Akita, Munetaka .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) :9567-9571
[65]   A chiral rhodium carboxamidate catalyst for enantioselective C-H amination [J].
Zalatan, David N. ;
Du Bois, J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (29) :9220-+
[66]  
Zhang Y.-Q., 2018, ANGEW CHEM, V130, P13716
[67]   Synthesis of 1,3-Amino Alcohols by Hydroxy-Directed Aziridination and Aziridine Hydrosilylation [J].
Zhang, Yong-Qiang ;
Bohle, Fabian ;
Bleith, Robin ;
Schnakenburg, Gregor ;
Grimme, Stefan ;
Gansaeuer, Andreas .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (41) :13528-13532
[68]   Next Generation of Fluorine-Containing Pharmaceuticals, Compounds Currently in Phase II-III Clinical Trials of Major Pharmaceutical Companies: New Structural Trends and Therapeutic Areas [J].
Zhou, Yu ;
Wang, Jiang ;
Gu, Zhanni ;
Wang, Shuni ;
Zhu, Wei ;
Luis Acena, Jose ;
Soloshonok, Vadim A. ;
Izawa, Kunisuke ;
Liu, Hong .
CHEMICAL REVIEWS, 2016, 116 (02) :422-518
[69]   Nickel-Catalyzed Aminofluoroalkylative Cyclization of Styrenes with Ethyl Fluoroacetate and Anilines toward Fluoro-γ-Lactams [J].
Zhu, Fengxiang ;
Li, Ziyan ;
Wu, Xiao-Feng .
ORGANIC LETTERS, 2023, 25 (47) :8535-8539
[70]   Modern Approaches for Asymmetric Construction of Carbon-Fluorine Quaternary Stereogenic Centers: Synthetic Challenges and Pharmaceutical Needs [J].
Zhu, Yi ;
Han, Jianlin ;
Wang, Jiandong ;
Shibata, Norio ;
Sodeoka, Mikiko ;
Soloshonok, Vadim A. ;
Coelho, Jaime A. S. ;
Toste, F. Dean .
CHEMICAL REVIEWS, 2018, 118 (07) :3887-3964