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

被引：4
|
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
收藏
页码：548 / 558
页数：11
相关论文
共 50 条
  • [21] Rh(III)-Catalyzed Oxidative Annulation of 2-Phenylimidazo[1,2-a]pyridines with Alkynes: Mono versus Double C-H Activation
    Qi, Zisong
    Yu, Songjie
    Li, Xingwei
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (07) : 3471 - 3479
  • [22] Rh(III)-Catalyzed Sequential C-H Amination/Annulation Cascade Reactions: Synthesis of Multisubstituted Benzimidazoles
    Huang, Siqi
    Li, Huan
    Sun, Xiangying
    Xu, Linhua
    Wang, Lianhui
    Cui, Xiuling
    ORGANIC LETTERS, 2019, 21 (14) : 5570 - 5574
  • [23] Rh(III)-Catalyzed Aldehydic C-H Functionalization Reaction between Salicylaldehydes and Sulfoxonium Ylides
    Xu, Guo-Dong
    Huang, Kenneth L.
    Huang, Zhi-Zhen
    ADVANCED SYNTHESIS & CATALYSIS, 2019, 361 (14) : 3318 - 3323
  • [24] Rh(III)-Catalyzed C-H Activation with Allenes To Synthesize Conjugated Olefins
    Gong, Tian-Jun
    Su, Wei
    Liu, Zhao-Jing
    Cheng, Wan-Min
    Xiao, Bin
    Fu, Yao
    ORGANIC LETTERS, 2014, 16 (02) : 330 - 333
  • [25] Rhodium(III)-Catalyzed Enantioselective C-H Activation/Annulation of Ferrocenecarboxamides with Internal Alkynes
    Wang, Quannan
    Nie, Yu-Han
    Liu, Chen-Xu
    Zhang, Wen-Wen
    Wu, Zhi-Jie
    Gu, Qing
    Zheng, Chao
    You, Shu-Li
    ACS CATALYSIS, 2022, 12 (05) : 3083 - 3093
  • [26] Rh(III)-Catalyzed C-H Activation of Boronic Acid with Aryl Azide
    Xu, Shiyang
    Huang, Baoliang
    Qiao, Guanyu
    Huang, Ziyue
    Zhang, Zhen
    Li, Zongyang
    Wang, Peng
    Zhang, Zhenhua
    ORGANIC LETTERS, 2018, 20 (18) : 5578 - 5582
  • [27] Rhodium(III)-Catalyzed Oxidative Annulation of Amidines with Alkynes via Sequential C-H Bond Activation
    Meng, Yan-Yu
    Zhu, Wen-Jing
    Song, Yuan-Yuan
    Bu, Gang-Gang
    Zhang, Li-Juan
    Xu, Fen
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (08) : 1290 - 1294
  • [28] Synthesis of Polyheteroaromatic Compounds via Rhodium-Catalyzed Multiple C-H Bond Activation and Oxidative Annulation
    Peng, Shiyong
    Liu, Suna
    Zhang, Sai
    Cao, Shengyu
    Sun, Jiangtao
    ORGANIC LETTERS, 2015, 17 (20) : 5032 - 5035
  • [29] Rhodium(III)-Catalyzed C-H Activation/Annulation with Vinyl Esters as an Acetylene Equivalent
    Webb, Nicola J.
    Marsden, Stephen P.
    Raw, Steven A.
    ORGANIC LETTERS, 2014, 16 (18) : 4718 - 4721
  • [30] Direct Synthesis of Protoberberine Alkaloids by Rh-Catalyzed C-H Bond Activation as the Key Step
    Jayakumar, Jayachandran
    Cheng, Chien-Hong
    CHEMISTRY-A EUROPEAN JOURNAL, 2016, 22 (05) : 1800 - 1804
12345