Decarboxylative Functionalization of β,γ-Unsaturated Carboxylic Acids: New Perspective for the Synthesis of Functionalized Allylic Compounds

被引:1
|
作者
Yao, Zhen [1 ,2 ]
Xu, Lijin [1 ]
Shi, Qian [3 ]
机构
[1] Renmin Univ China, Dept Chem, Beijing 100872, Peoples R China
[2] Guizhou Univ Tradit Chinese Med, Sch Pharm, Guiyang 550025, Peoples R China
[3] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Peoples R China
基金
中国国家自然科学基金;
关键词
allyl compound; allylating reagent; allylation; decarboxylation; beta; gamma-unsaturated carboxylic acid; CARBONYL-COMPOUNDS; IODINE; ALLYLATION; CATALYSIS;
D O I
10.1002/cctc.202300639
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
Due to the versatile reactivity of allyl moieties for further transformations and their omnipresence in biologically and pharmaceutically active molecules, significant efforts have been devoted to the efficient introduction of such groups into organic compounds. Although a large variety of allylating reagents have been successfully developed, development of new, efficient and environmentally benign allylating reagents remains in high demand. Recently, easily accessible beta,gamma-unsaturated carboxylic acids have been explored as promising allylating agents in decarboxylative allylation reactions. This type of transformation provides facile access to various functionalized allyl compounds including those that are difficult to prepare using the classic allylating reagents with high efficiency and regiocontrol, and can be rendered enantioselective by choosing a suitable catalyst precursor and chiral ligand. Moreover, utilizing such allylating reagents allows for the discovery of novel transformations, especially under visible light photocatalysis.
引用
收藏
页数:7
相关论文
共 50 条
  • [21] Functionalization of Alkyl Groups Adjacent to Azoles: Application to the Synthesis of α-Functionalized Carboxylic Acids
    Singh, Anupam Kumar
    Shinde, Rupali Dasharath
    Kumar, Jogendra
    Bhadra, Sukalyan
    SYNLETT, 2023, 34 (06) : 561 - 571
  • [22] C(sp)–H bond functionalization of non-cyclic ethers by decarboxylative oxidative coupling with α,β-unsaturated carboxylic acids
    Tong Zhang
    XingWang Lan
    YuQiang Zhou
    NaiXing Wang
    YueHua Wu
    Yalan Xing
    JiaLong Wen
    Science China(Chemistry), 2018, (02) : 180 - 183
  • [23] Photo-Promoted Decarboxylative Alkylation of α,β-Unsaturated Carboxylic Acids with ICH2CN for the Synthesis of β,γ-Unsaturated Nitriles
    Pan, Chunxiang
    Yang, Chunhui
    Li, Kangkui
    Zhang, Keyang
    Zhu, Yuanbin
    Wu, Shiyuan
    Zhou, Yongyun
    Fan, Baomin
    ORGANIC LETTERS, 2021, 23 (18) : 7188 - 7193
  • [24] TsNBr2 promoted decarboxylative bromination of α,β-unsaturated carboxylic acids
    Hazarika, Debojit
    Phukan, Prodeep
    TETRAHEDRON LETTERS, 2018, 59 (52) : 4593 - 4596
  • [25] Iron-Mediated Decarboxylative Trifluoromethylation of α,β-Unsaturated Carboxylic Acids with Trifluoromethanesulfinate
    Patra, Tuhin
    Deb, Arghya
    Manna, Srimanta
    Sharma, Upendra
    Maiti, Debabrata
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2013, 2013 (24) : 5247 - 5250
  • [26] Copper-Catalyzed Decarboxylative Difluoroalkylation and Perfluoroalkylation of α,β-Unsaturated Carboxylic Acids
    Lai, Yin-Long
    Lin, Dian-Zhao
    Huang, Jing-Mei
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01): : 597 - 605
  • [27] CuSO4-Mediated Decarboxylative Difluoroacetamidation of α,β-Unsaturated Carboxylic Acids
    Chen, Qiao
    Wang, Chao
    Zhou, Jiawei
    Wang, Yanan
    Xu, Zhaoqing
    Wang, Rui
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (06): : 2639 - 2645
  • [28] Room temperature decarboxylative trifluoromethylation of α,β-unsaturated carboxylic acids by photoredox catalysis
    Xu, Pan
    Abdukader, Ablimit
    Hu, Kaidong
    Cheng, Yixiang
    Zhu, Chengjian
    CHEMICAL COMMUNICATIONS, 2014, 50 (18) : 2308 - 2310
  • [29] Enabling α -Functionalization of Carboxylic Acids by Boron Compounds
    Shimizu, Yohei
    Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry, 2024, 82 (08): : 802 - 813
  • [30] Enabling α ―Functionalization of Carboxylic Acids by Boron Compounds
    Shimizu, Yohei
    JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN, 2024, 82 (08) : 802 - 813