Rh(III)-Catalyzed Oxidative C-H Activation/Annulation of Salicylaldehydes with Masked Enynes for the Synthesis of Chromones

被引：3
|
作者：
Li, Bo [1 ,2 ]
Zhu, Jianping [1 ,2 ]
Zheng, Xia [1 ,2 ]
Ti, Wenqing [1 ,2 ]
Huang, Yue [3 ]
Yao, Hequan [1 ,2 ]
机构：
[1] China Pharmaceut Univ, State Key Lab Nat Med SKLNM, Nanjing 210009, Peoples R China
[2] China Pharmaceut Univ, Sch Pharm, Dept Med Chem, Nanjing 210009, Peoples R China
[3] China Pharmaceut Univ, Sch Sci, Dept Organ Chem, Nanjing 210009, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 01期
基金：
中国国家自然科学基金;
关键词：
ONE-POT SYNTHESIS; ANTIANAPHYLACTIC AGENTS; CATALYZED ALKENE; RHODIUM; CLEAVAGE; ALKYNES; ANNULATION; ALDEHYDES; HYDROACYLATION; CYCLOPROPENES;
D O I：
10.1021/acs.joc.2c02557
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A rhodium(III)-catalyzed oxidative C-H activation/annulation of salicylaldehydes with propargylic acetates has been developed for the regioselective synthesis of 3-vinyl chromones in good yields with broad functional group tolerance. 3-Vinyl chromones were converted into biologically active benzo[c]xanthone by I2-mediated oxidative electrocyclization.
引用
下载
收藏
页码：548 / 558
页数：11
相关论文
共 50 条
  • [1] Rh(iii)-Catalyzed C-H activation/annulation of salicylaldehydes with sulfoxonium ylides for the synthesis of chromones
    Cai, Libo
    Zhu, Xiaoyi
    Chen, Jiayi
    Lin, Aijun
    Yao, Hequan
    ORGANIC CHEMISTRY FRONTIERS, 2019, 6 (21): : 3688 - 3692
  • [2] Theoretical Investigations on the Rh(III)-Catalyzed Oxidative C-H Activation/Annulation of Salicylaldehydes with Masked Enynes: Mechanism Insights and Regioselectivity Origins
    Xiang, Xin
    Wei, Wei
    Zhao, Zeng-Xia
    Zhang, Hong-Xing
    ACS OMEGA, 2023, 8 (47): : 45109 - 45114
  • [3] Rh(III)-Catalyzed Enaminone-Directed Alkenyl C-H Activation for the Synthesis of Salicylaldehydes
    Qi, Bing
    Guo, Shan
    Zhang, Wenjing
    Yu, Xiaolong
    Song, Chao
    Zhu, Jin
    ORGANIC LETTERS, 2018, 20 (13) : 3996 - 3999
  • [4] Practical synthesis of isocoumarins via Rh(III)-catalyzed C-H activation/annulation cascade
    Gao, Qian-Ci
    Li, Yi-Fei
    Xuan, Jun
    Hu, Xiao-Qiang
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2023, 19 : 100 - 106
  • [5] On-Water Cp*Ir(III)-Catalyzed C-H Functionalization for the Synthesis of Chromones through Annulation of Salicylaldehydes with Diazo-Ketones
    Debbarma, Suvankar
    Sk, Md Raja
    Modak, Biswabrata
    Maji, Modhu Sudan
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10): : 6207 - 6216
  • [6] Controllable Rh(III)-Catalyzed Annulation between Salicylaldehydes and Diazo Compounds: Divergent Synthesis of Chromones and Benzofurans
    Sun, Peng
    Gao, Shang
    Yang, Chi
    Guo, Songjin
    Lin, Aijun
    Yao, Hequan
    ORGANIC LETTERS, 2016, 18 (24) : 6464 - 6467
  • [7] Rh(III)-Catalyzed C-H Activation/Annulation for the Construction of Quinolizinones and Indolizines
    Hou, Xinjiao
    Wang, Run
    Fang, Feifei
    Qu, Zhiyan
    Zhou, Jianhui
    Yu, Ting
    Wang, Dechuan
    Liu, Hong
    Zhou, Yu
    ORGANIC LETTERS, 2024, 26 (21) : 4451 - 4456
  • [8] Cp*Ir(III)-Catalyzed C-H/O-H Functionalization of Salicylaldehydes for the Synthesis of Chromones at Room Temperature
    Lade, Dhanaji M.
    Aher, Yogesh N.
    Pawar, Amit B.
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (14): : 9188 - 9195
  • [9] Synthesis of Spiropentadiene Pyrazolones by Rh(III)-Catalyzed Formal sp3 C-H Activation/Annulation
    Zheng, Jivan
    Li, Panpan
    Gu, Meng
    Lin, Aijun
    Yao, Hequan
    ORGANIC LETTERS, 2017, 19 (11) : 2829 - 2832
  • [10] Rh(III)-Catalyzed Regioselective Functionalization of C-H Bonds of Naphthylcarbamates for Oxidative Annulation with Alkynes
    Zhang, Xuan
    Si, Weili
    Bao, Ming
    Asao, Naoki
    Yamamoto, Yoshinori
    Jin, Tienan
    ORGANIC LETTERS, 2014, 16 (18) : 4830 - 4833
12345