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
来源：
ORGANIC LETTERS | 2023年 / 25卷 / 13期
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
  • [41] Nickel-Catalyzed Reductive Dicarbofunctionalization of Alkenes
    Garcia-Dominguez, Andres
    Li, Zhaodong
    Nevado, Cristina
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (20) : 6835 - 6838
  • [42] Photoelectrochemical nickel-catalyzed carboacylation/silanoylation of alkenes with unactivated C/Si-H bonds
    Wang, Lanfen
    Huo, Xiangyu
    He, Xiaozhi
    Ackermann, Lutz
    Wang, Dingyi
    [J]. GREEN CHEMISTRY, 2024, 26 (14) : 8315 - 8322
  • [43] Neutral nickel-catalyzed dehydrosulfonylation of unactivated allylic alcohols under mild conditions
    Yang, Yahui
    Zhu, Haibo
    Gong, Bozhen
    Yang, Hong
    Fan, Qiangwen
    Le, Zhang-Gao
    Xie, Zongbo
    [J]. CHEMICAL COMMUNICATIONS, 2024, 60 (18) : 2516 - 2519
  • [44] Visible-Light-Induced Nickel-Catalyzed Cross-Coupling with Alkylzirconocenes from Unactivated Alkenes
    Gao, Yadong
    Yang, Chao
    Bai, Songlin
    Liu, Xiaolei
    Wu, Qingcui
    Wang, Jing
    Jiang, Chao
    Qi, Xiangbing
    [J]. CHEM, 2020, 6 (03): : 675 - 688
  • [45] Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
    Xian Zhao
    Hai-Yong Tu
    Lei Guo
    Shengqing Zhu
    Feng-Ling Qing
    Lingling Chu
    [J]. Nature Communications, 9
  • [46] Nickel-Catalyzed Hydrofluorination in Unactivated Alkenes: Regio- and Enantioselective C-F Bond Formation
    Lee, Changseok
    Kim, Minseok
    Han, Seunghoon
    Kim, Dongwook
    Hong, Sungwoo
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (13) : 9375 - 9384
  • [47] Nickel-catalyzed cycloadditions of unactivated carbonyls with unsaturated hydrocarbons
    Tekavec, TN
    Louie, J
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2005, 230 : U3227 - U3228
  • [48] Intermolecular selective carboacylation of alkenes via nickel-catalyzed reductive radical relay
    Zhao, Xian
    Tu, Hai-Yong
    Guo, Lei
    Zhu, Shengqing
    Qing, Feng-Ling
    Chu, Lingling
    [J]. NATURE COMMUNICATIONS, 2018, 9
  • [49] Hydrophosphinylation of Unactivated Terminal Alkenes Catalyzed by Nickel Chloride
    Ortial, Stephanie
    Fisher, Henry C.
    Montchamp, Jean-Luc
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (13): : 6599 - 6608
  • [50] Nickel-Catalyzed Asymmetric Reductive Dicarbamoylation of Alkenes
    Wu, Jiaoyang
    Wang, Chuan
    [J]. ORGANIC LETTERS, 2021, 23 (16) : 6407 - 6411
12345