Directed Nickel-Catalyzed Selective Arylhydroxylation of Unactivated Alkenes under Air

被引:2
|
作者
Wang, Yihua [1 ]
Lin, Cong [1 ]
Zhang, Zongxu [1 ]
Shen, Liang [2 ]
Zou, Boya [1 ]
机构
[1] Jiangxi Sci & Technol Normal Univ, Coll Chem & Chem Engn, Nanchang 330013, Peoples R China
[2] Jiangxi Sci & Technol Normal Univ, Coll Chem & Chem Engn, Jiangxi Engn Lab Waterborne Coatings, Nanchang 330013, Peoples R China
基金
中国国家自然科学基金;
关键词
ARYLBORONIC ACIDS; OXYARYLATION; FUNCTIONALIZATION; COMPLEXES; OXINDOLES; DIOXYGEN; STYRENES; OLEFINS; ACCESS;
D O I
10.1021/acs.orglett.3c00085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An expeditious and novel nickel-catalyzed selective arylhydroxylation of unactivated alkenes with arylboronic acids was developed. This protocol is compatible with fi,y- and y,(5-alkene amides, including traditionally challenging internal alkenes, to provide important fi-arylethylalcohol scaffolds. The free hydroxyl group in the final product could be smoothly further transformed into other functional groups. Control experiments indicated that the oxygen atom of the hydroxyl group in the product is derived from the oxygen in the air.
引用
收藏
页码:2172 / 2177
页数:6
相关论文
共 50 条
  • [1] Directed Nickel-Catalyzed Regio- and Diastereoselective Arylamination of Unactivated Alkenes
    Xie, Leipeng
    Wang, Shenghao
    Zhang, Lanlan
    Zhao, Lei
    Luo, Chun
    Mu, Linping
    Wang, Xiuguang
    Wang, Chao
    [J]. SYNLETT, 2022, 33 (04) : A40 - A43
  • [2] Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes
    Xie, Leipeng
    Wang, Shenghao
    Zhang, Lanlan
    Zhao, Lei
    Luo, Chun
    Mu, Linping
    Wang, Xiuguang
    Wang, Chao
    [J]. NATURE COMMUNICATIONS, 2021, 12 (01)
  • [3] Directed nickel-catalyzed regio- and diastereoselective arylamination of unactivated alkenes
    Leipeng Xie
    Shenghao Wang
    Lanlan Zhang
    Lei Zhao
    Chun Luo
    Linping Mu
    Xiuguang Wang
    Chao Wang
    [J]. Nature Communications, 12
  • [4] Nickel-Catalyzed Stereoselective Arylboration of Unactivated Alkenes
    Logan, Kaitlyn M.
    Sardini, Stephen R.
    White, Sean D.
    Brown, M. Kevin
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2018, 140 (01) : 159 - 162
  • [5] Nickel-Catalyzed Asymmetric Reductive Arylalkylation of Unactivated Alkenes
    Jin, Youxiang
    Wang, Chuan
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (20) : 6722 - 6726
  • [6] Nickel-Catalyzed Asymmetric Reductive Arylbenzylation of Unactivated Alkenes
    Jin, Youxiang
    Yang, Haobo
    Wang, Chuan
    [J]. ORGANIC LETTERS, 2020, 22 (07) : 2724 - 2729
  • [7] Nickel-Catalyzed 8-Aminoquinoline Directed Reductive Dialkylcyclization/Homodialkylation of Unactivated Alkenes
    Lu, Lingyi
    Sui, Jing
    Huang, Shanshan
    Xiong, Biao
    Zeng, Xiaobao
    Qiu, Xiaodong
    Zhang, Yanan
    [J]. ORGANIC LETTERS, 2023, 25 (43) : 7800 - 7804
  • [8] Directed Asymmetric Nickel-Catalyzed Reductive 1,2-Diarylation of Electronically Unactivated Alkenes
    Dong, Zhan
    Tang, Qiongyao
    Xu, Changyu
    Chen, Li
    Ji, Haiting
    Zhou, Sitian
    Song, Liangliang
    Chen, Liang-An
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2023, 62 (13)
  • [9] Nickel-Catalyzed anti-Markovnikov Hydrodifluoroalkylation of Unactivated Alkenes
    Yin, Li-Ming
    Sun, Meng-Chan
    Si, Xiao-Ju
    Yang, Dandan
    Song, Mao-Ping
    Niu, Jun-Long
    [J]. ORGANIC LETTERS, 2022, 24 (04) : 1083 - 1087
  • [10] Nickel-Catalyzed Difunctionalization of Unactivated Alkenes Initiated by Unstabilized Enolates
    Huang, David
    Olivieri, Diego
    Sun, Yang
    Zhang, Pengpeng
    Newhouse, Timothy R.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (41) : 16249 - 16254