Iodine-mediated 1,2-aryl migration of primary benzhydryl amines

被引:1
|
作者
Du, Yangxu
Hou, Jiao
Lu, Qing
Hao, Wei
Yu, Wenquan [1 ]
Chang, Junbiao [1 ]
机构
[1] Zhengzhou Univ, Green Catalysis Ctr, Zhengzhou 450001, Henan, Peoples R China
基金
中国国家自然科学基金;
关键词
OXIDATIVE REARRANGEMENT; MOLECULAR REARRANGEMENT; BECKMANN REARRANGEMENT;
D O I
10.1039/d1nj02932k
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An iodine-mediated 1,2-aryl migration reaction of primary benzhydryl amines under transition metal-free conditions has been achieved. The crude imines generated by this rearrangement reaction can be directly transformed into various aromatic secondary amine derivatives via reduction or addition reactions. This sequential synthetic process is operationally simple and can be successfully conducted on a gram scale.
引用
收藏
页码:16223 / 16226
页数:4
相关论文
共 50 条
  • [1] Advances in Radical Mediated 1,2-Aryl Migration Reactions of α,α-Diarylallyl Alcohols
    Zhang Jiantao
    Deng Yawen
    Mo Nuolin
    Chen Lianfen
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (02) : 426 - 435
  • [2] 1,2-ARYL MIGRATION ONTO ACYLNITRENIUM IONS
    SHERADSKY, T
    AVRAMOVICIGRISARU, S
    [J]. TETRAHEDRON LETTERS, 1978, (26) : 2325 - 2326
  • [3] 1,2-ARYL MIGRATION IN BIOSYNTHESIS OF ROTENONE AND AMORPHIN
    CROMBIE, L
    THOMAS, MB
    [J]. CHEMICAL COMMUNICATIONS, 1965, (08) : 155 - &
  • [4] Chemoselective cycloisomerization of O-alkenylbenzamides via concomitant 1,2-aryl migration/elimination mediated by hypervalent iodine reagents
    Jiaxin He
    Feng-Huan Du
    Chi Zhang
    Yunfei Du
    [J]. Communications Chemistry, 6
  • [5] Chemoselective cycloisomerization of O-alkenylbenzamides via concomitant 1,2-aryl migration/elimination mediated by hypervalent iodine reagents
    He, Jiaxin
    Du, Feng-Huan
    Zhang, Chi
    Du, Yunfei
    [J]. COMMUNICATIONS CHEMISTRY, 2023, 6 (01)
  • [6] Aryl iodine-catalysed divergent synthesis of isobenzofuranones and isocoumarins via oxidative 1,2-aryl migration/elimination
    He, Jiaxin
    Zhang, Jingran
    Li, Xuemin
    Shi, Haofeng
    Du, Yunfei
    [J]. CHEMICAL COMMUNICATIONS, 2022, 58 (65) : 9096 - 9099
  • [7] Lactonization with concomitant 1,2-aryl migration and alkoxylation mediated by dialkoxyphenyl iodides generated in situ
    Zhang, Jingran
    Jalil, Ayesha
    He, Jiaxin
    Yu, Zhenyang
    Cheng, Yifu
    Li, Guangchen
    Du, Yunfei
    Zhao, Kang
    [J]. CHEMICAL COMMUNICATIONS, 2021, 57 (60) : 7426 - 7429
  • [8] Iodine-Mediated Aryl C-H Amination for the Synthesis of Benzimidazoles and Pyrido[1,2-a]benzimidazoles
    Lv, Zhigang
    Liu, Jing
    Wei, Wei
    Wu, Jie
    Yu, Wenquan
    Chang, Junbiao
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (17) : 2759 - 2766
  • [9] Visible light-mediated arylalkylation of allylic alcohols through concomitant 1,2-aryl migration
    Huang, Hong-Li
    Yan, Hang
    Yang, Chao
    Xia, Wujiong
    [J]. CHEMICAL COMMUNICATIONS, 2015, 51 (23) : 4910 - 4913
  • [10] Fe(III)-mediated isomerization of α, α-diarylallylic alcohols to ketones via radical 1,2-aryl migration
    Deng, Ziyang
    Chen, Changwei
    Cui, Sunliang
    [J]. RSC ADVANCES, 2016, 6 (96): : 93753 - 93755