Palladium(II)-Catalyzed Remote meta-C-H Functionalization of Arenes Enabled by Multitasking Oxyamides as the Linker

被引:0
作者
Zhu, Yue-Lu [1 ]
Sun, Qiu-Xue [1 ]
Feng, Jin-Shuo [1 ]
Shao, You-Dong [1 ]
Chen, Jiao [2 ,3 ]
机构
[1] Heze Univ, Sch Chem & Chem Engn, Heze 274015, Shandong, Peoples R China
[2] Northwest Univ, Coll Chem & Mat Sci, Xian 710127, Shaanxi, Peoples R China
[3] Northwest Univ, Coll Life Sci, Xian 710069, Shaanxi, Peoples R China
关键词
OLEFINATION; ACTIVATION; TEMPLATE; BONDS; ACETOXYLATION; ACID; IRON;
D O I
10.1021/acs.orglett.3c01101
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzedolefination of meta-C-Hbonds in arenes containing oxyamides using a nitrile template as thedirecting group has been established. The methodology exhibited high meta-selectivity and tolerated different functional groupssuch as benzyloxyamides and olefin substrates. The desired productswere obtained in good yields. This approach enabled the modificationof natural products and drugs and was also applicable on the gram-scale.Furthermore, the directing template was readily removed by selectivecleavage of the amide bond or the O-N bond to obtain meta-functionalized hydroxylamines and benzyl alcohols.The proposed method holds great potential for the design of noveldrugs.
引用
收藏
页码:4416 / 4421
页数:6
相关论文
共 50 条
[41]   Palladium-Catalyzed Double C-H Functionalization of Arenes at the Positions ortho and meta to Their Directing Group: Concise Synthesis of Benzocyclobutenes [J].
Nanjo, Takeshi ;
Tsukano, Chihiro ;
Takemoto, Yoshiji .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2016, 64 (09) :1384-1392
[42]   Rh(III)-Catalyzed meta-C-H Alkenylation with Alkynes [J].
Xu, Hua-Jin ;
Kang, Yan-Shang ;
Shi, Hang ;
Zhang, Ping ;
Chen, You-Ke ;
Zhang, Bing ;
Liu, Zhi-Qiang ;
Zhao, Jing ;
Sun, Wei-Yin ;
Yu, Jin-Quan ;
Lu, Yi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (01) :76-79
[43]   Transition-metal-catalyzed remote meta-C-H alkylation and alkynylation of aryl sulfonic acids enabled by an indolyl template [J].
Zhang, Pengfei ;
Ma, Qingxue ;
Jiang, Zhiwei ;
Xu, Xiaohua ;
Jin, Zhong .
CHINESE CHEMICAL LETTERS, 2024, 35 (08)
[44]   Palladium-Catalyzed meta-Selective C-H Functionalization by Noncovalent H-Bonding Interaction [J].
Li, Guoshuai ;
Yan, Yifei ;
Zhang, Pengfei ;
Xu, Xiaohua ;
Jin, Zhong .
ACS CATALYSIS, 2021, 11 (16) :10460-10466
[45]   Ligand-enabled ruthenium-catalyzed meta-C-H alkylation of (hetero)aromatic carboxylic acids [J].
Luo, Xianglin ;
Hou, Peichao ;
Shen, Jiayi ;
Kuang, Yifeng ;
Sun, Fengchao ;
Jiang, Huanfeng ;
Goossen, Lukas J. ;
Huang, Liangbin .
NATURE COMMUNICATIONS, 2024, 15 (01)
[46]   Sequential Functionalization of meta-C-H and ipso-C-O Bonds of Phenols [J].
Xu, Jiancong ;
Chen, Jingjing ;
Gao, Feng ;
Xie, Shuguang ;
Xu, Xiaohua ;
Jin, Zhong ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (05) :1903-1907
[47]   Conformation-induced remote meta-C-H activation of amines [J].
Tang, Ri-Yuan ;
Li, Gang ;
Yu, Jin-Quan .
NATURE, 2014, 507 (7491) :215-220
[48]   Ligand-Promoted meta-C-H Functionalization of Benzylamines [J].
Wang, Peng ;
Farmer, Marcus E. ;
Yu, Jin-Quan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (18) :5125-5129
[49]   Palladium-Catalyzed Distal m-C-H Functionalization of Arylacetic Acid Derivatives [J].
Srinivas, Dasari ;
Satyanarayana, Gedu .
ORGANIC LETTERS, 2021, 23 (19) :7353-7358
[50]   Emergence of Pyrimidine-Based meta-Directing Group: Journey from Weak to Strong Coordination in Diversifying meta-C-H Functionalization [J].
Dutta, Uttam ;
Maiti, Debabrata .
ACCOUNTS OF CHEMICAL RESEARCH, 2022, 55 (03) :354-372