Organocatalyzed cross-dehydrogenative coupling for C(sp3)-O bonds formation: a rapid access to -aminoxyl isochromans

被引:8
|
作者
Zhou, Yuli [1 ]
Chen, Jingwen [1 ]
Elsayed, Ahmed Ali [1 ,2 ]
Zhang, Zhiguo [1 ]
Bao, Zongbi [1 ]
Yang, Qiwei [1 ]
Yang, Yiwen [1 ]
Ren, Qilong [1 ]
机构
[1] Zhejiang Univ, Coll Chem & Biol Engn, Minist Educ, Key Lab Biomass Chem Engn, Zheda Rd 38, Hangzhou 310027, Zhejiang, Peoples R China
[2] Natl Res Ctr, Dept Photochem, Tahrir St, Giza, Egypt
基金
中国国家自然科学基金; 国家重点研发计划;
关键词
Organocatalysis; -Aminoxyl isochromans; C-O bond formation; TBAI; TBHP;
D O I
10.1007/s10562-018-2640-9
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
Tetrabutyl ammonium iodide catalyzed cross-dehydrogenative coupling reaction between -C(sp(3))-H of isochromans and N-hydroxyphathalimide has been achieved using tert-butylhydroxyperoxide as theterminal oxidant. This method offers rapid access to prevalent -aminoxyl isochroman architectures. A diverse of synthetic isochromans was tolerated with this protocol, giving the corresponding product in moderate to good yields. [GRAPHICS] .
引用
收藏
页码:574 / 579
页数:6
相关论文
共 50 条
  • [1] Organocatalyzed cross-dehydrogenative coupling for C(sp3)–O bonds formation: a rapid access to α-aminoxyl isochromans
    Yuli Zhou
    Jingwen Chen
    Ahmed Ali Elsayed
    Zhiguo Zhang
    Zongbi Bao
    Qiwei Yang
    Yiwen Yang
    Qilong Ren
    Catalysis Letters, 2019, 149 : 574 - 579
  • [2] Electrochemical C(sp3)-C(sp3) cross-dehydrogenative coupling: enabling access to 9-substituted fluorescent acridanes
    Roy, Shantonu
    Karmakar, Sudip
    Mondal, Imtiaj
    Naskar, Koushik
    Sarkar, Writhabrata
    Deb, Indubhusan
    CHEMICAL COMMUNICATIONS, 2023, 59 (59) : 9074 - 9077
  • [3] Nickel-Catalyzed Cross-Dehydrogenative Coupling of α-C(sp3)-H Bonds in N-Methylamides with C(sp3)-H Bonds in Cyclic Alkanes
    Li, Ze-Lin
    Sun, Kang-Kang
    Cai, Chun
    ORGANIC LETTERS, 2018, 20 (20) : 6420 - 6424
  • [4] Metal-free oxidative cross-dehydrogenative coupling of quinones with benzylic C(sp3)-H bonds
    Dong, Yu
    Yang, Jian
    He, Shuai
    Shi, Zhi-Chuan
    Wang, Yu
    Zhang, Xiao-Mei
    Wang, Ji-Yu
    RSC ADVANCES, 2019, 9 (47) : 27588 - 27592
  • [5] Iron-catalyzed construction of cyanomethylated thiohydantoins by cross-dehydrogenative C(sp3)-C(sp3) coupling
    Morja, Mayur I.
    Moradiya, Riddhi B.
    Makwana, Bhavik S.
    Chikhalia, Kishor H.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (03) : 449 - 457
  • [6] Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp3)–H bonds
    Fufang Wu
    Xuanzhen Han
    Xuejian Li
    Xiaobao Shen
    Chang Wang
    Zhimei Tian
    Bin Cheng
    Jingbin Zhang
    Liangquan Sheng
    Hongbin Zhai
    Communications Chemistry, 4
  • [7] Electricity-driven enantioselective cross-dehydrogenative coupling of two C(sp3 )-H bonds enabled by organocatalysis
    Chen, Yuemin
    Wu, Yunqi
    Wang, Guoao
    Cui, Feihu
    Tang, Haitao
    Pan, Yingming
    CHINESE CHEMICAL LETTERS, 2024, 35 (09)
  • [8] Iodine(III) promotes cross-dehydrogenative coupling of N-hydroxyphthalimide and unactivated C(sp3)-H bonds
    Wu, Fufang
    Han, Xuanzhen
    Li, Xuejian
    Shen, Xiaobao
    Wang, Chang
    Tian, Zhimei
    Cheng, Bin
    Zhang, Jingbin
    Sheng, Liangquan
    Zhai, Hongbin
    COMMUNICATIONS CHEMISTRY, 2021, 4 (01)
  • [9] Nickel-Catalyzed Regioselective Cross-Dehydrogenative Coupling of Inactive C(sp3)-H Bonds with Indole Derivatives
    Jin, Li-Kun
    Wan, Li
    Feng, Jie
    Cai, Chun
    ORGANIC LETTERS, 2015, 17 (19) : 4726 - 4729
  • [10] Transition-metal-free access to benzyl ethers via aerobic cross-dehydrogenative coupling of benzylic C(sp3)-H bonds with alcohols
    Zhang, Xiao
    Li, Wenjie
    Yu, Yang
    Luo, Min
    Bai, Hua
    Shi, Lei
    Li, Hao
    GREEN CHEMISTRY, 2024, 26 (04) : 2207 - 2212