Carboxylation of Alkenes with CO2 via Photocatalytic Cleavage of C=C Double Bonds

被引:0
|
作者
Yuan, Pan-Feng [1 ]
Meng, Qing-Yuan [1 ,2 ]
机构
[1] Chinese Acad Sci, Inst Chem, Beijing Natl Lab Mol Sci, CAS Key Lab Mol Recognit & Funct, 2,1St North St, Beijing 100190, Peoples R China
[2] Univ Chinese Acad Sci, 80 Zhongguancun East Rd, Beijing 100049, Peoples R China
基金
中国国家自然科学基金;
关键词
alkenes; carbon dioxide; carboxylation; photocatalysis; synthetic methods; CATALYZED REDUCTIVE CARBOXYLATION; C-N BONDS; CARBON-DIOXIDE; VISIBLE-LIGHT; REGIOSELECTIVE HYDROCARBOXYLATION; SELECTIVE CARBOXYLATION; AMINOALKYL RADICALS; OXIDATIVE CLEAVAGE; PHOTOREDOX; ALKYNES;
D O I
10.1055/s-0043-1763755
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The cleavage of double bonds in alkenes constitutes an integral process in converting feedstock materials into high-value synthetic intermediates. Well-known examples such as the oxidative cleavage of olefins and olefin metathesis only facilitate the synthesis of oxygen-containing compounds and the recombination of olefins. Therefore, it is appealing to extend C=C double bond cleavage to yield more abundant transformations. Herein, we report a novel photocatalytic approach for the deconstructive carboxylation of alkenes with CO(2 )for the synthesis of carboxylic acids in the absence of transition metals. Compared with reported carboxylations with CO2 during which carbon numbers are typically increased, we achieve the exchange of carbon di-oxide with one of the carbons of the alkene double bond, thus providing carboxylic acids with unchanged carbon numbers when terminal alkenes are used.
引用
收藏
页数:10
相关论文
共 50 条
  • [41] Electro-reductive carboxylation of C-Cl bonds in unactivated alkyl chlorides and polyvinyl chloride with CO2
    Li, Li
    Yan, Zhi-Xin
    Ran, Chuan-Kun
    Liu, Yi
    Zhang, Shuo
    Gao, Tian-Yu
    Dai, Long-Fei
    Liao, Li-Li
    Ye, Jian-Heng
    Yu, Da-Gang
    CHINESE CHEMICAL LETTERS, 2024, 35 (12)
  • [42] Visible Light-Induced Carboxylation of Alkenes via Cleavage of Carbon-Carbon Double Bond
    Wu Yang
    Xia Jibao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2024, 44 (04) : 1377 - 1378
  • [43] O/C bond cleavage of CO2 by NiI
    Fullmer, Benjamin C.
    Fan, Hongjun
    Pink, Maren
    Caulton, Kenneth G.
    INORGANIC CHEMISTRY, 2008, 47 (06) : 1865 - 1867
  • [44] NICKEL-COMPLEX-PROMOTED CARBOXYLATION OF HALOARENES INVOLVING INSERTION OF CO2 INTO NI-II-C BONDS
    OSAKADA, K
    SATO, R
    YAMAMOTO, T
    ORGANOMETALLICS, 1994, 13 (11) : 4645 - 4647
  • [45] A Study on C-H Carboxylation Reaction of Terminal Alkynes with CO2 in Supercritical CO2
    Li, Fawang
    Suo, Quanling
    Hong, Hailong
    Zhu, Ning
    Wang, Yaqi
    Han, Limin
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2014, 34 (10) : 2172 - 2177
  • [46] Incorporation of CO2 into organosilicon compounds via C-Si bond cleavage
    Xu, Wei
    Ebadi, Abdol Ghaffar
    Toughani, Mohsen
    Vessally, Esmail
    JOURNAL OF CO2 UTILIZATION, 2021, 43
  • [47] Carbenes as Electron-Pair Donors To CO2 for C•••C Tetrel Bonds and C-C Covalent Bonds
    Del Bene, Janet E.
    Alkorta, Ibon
    Elguero, Jose
    JOURNAL OF PHYSICAL CHEMISTRY A, 2017, 121 (20): : 4039 - 4047
  • [48] Cleavage and Carboxylation of C-N Bonds in Cyclic Amines via Consecutive Photo-induced Electron Transfer
    Zhu, Mengwei
    Xia, Jibao
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2023, 43 (05) : 1885 - 1886
  • [49] Photocatalytic oxidative cleavage of aryl alkene C=C bonds using a uranyl cation
    Tang, Song-Bai
    Zhang, Shu-Yun
    Li, Wen-Jing
    Jiang, Yan-Xin
    Wang, Zi-Xin
    Long, Bo
    Su, Jing
    ORGANIC CHEMISTRY FRONTIERS, 2023, 10 (20) : 5130 - 5137
  • [50] Recent advances in homogeneous photocatalytic carboxylation incorporated with CO2
    Wu, Zhong-Qian
    Fan, Zhengning
    Xi, Chanjuan
    CHINESE SCIENCE BULLETIN-CHINESE, 2021, 66 (07): : 773 - 797