Transition metal-free synthesis of α-aryl ketones via oxyallyl cation capture with arylboronic acids

被引:12
|
作者
Huang, Wei-Hua [1 ]
Huang, Gong-Bin [1 ]
Zhu, Wen-Run [1 ]
Weng, Jiang [1 ]
Lu, Gui [1 ]
机构
[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangdong Prov Key Lab New Drug Design & Evaluat, Guangzhou 510006, Peoples R China
来源
ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 17期
基金
中国国家自然科学基金;
关键词
4+3 CYCLOADDITION REACTION; CROSS-COUPLINGS; BORONIC ACIDS; ARYLATION; INTERMEDIATE; CARBON; FUNCTIONALIZATION; ACTIVATION; REACTIVITY; FLUORINE;
D O I
10.1039/d0qo00447b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein, we describe a novel transition metal-free, umpolung strategy for the alpha-arylation of ketones by capturing transient oxyallyl cations with arylboronic acids. A variety of alpha-arylated ketones were obtained in moderate to good yields with broad substrate tolerance under simple reaction conditions. This process provides a complementary strategy compared with traditional transition metal-catalyzed methods.
引用
收藏
页码:2480 / 2485
页数:6
相关论文
共 50 条
  • [31] Recent advances in the transition metal-free synthesis of heterocycles from α,β-unsaturated ketones
    Ashitha, Kizhakkan Thiruthi
    Krishna, Ajay M. S.
    Basavaraja, D.
    Somappa, Sasidhar B.
    ORGANIC CHEMISTRY FRONTIERS, 2022, 9 (19) : 5306 - 5358
  • [32] Metal-free oxidative cross-coupling of diazirines with arylboronic acids
    Wu, Guojiao
    Zhao, Xia
    Ji, Wenzhi
    Zhang, Yan
    Wang, Jianbo
    CHEMICAL COMMUNICATIONS, 2016, 52 (09) : 1961 - 1963
  • [33] Metal-Free Synthesis of Aryl Esters from Carboxylic Acids and Diaryliodonium Salts
    Petersen, Tue B.
    Khan, Rehan
    Olofsson, Berit
    ORGANIC LETTERS, 2011, 13 (13) : 3462 - 3465
  • [34] Metal-Free Synthesis of Aryl Ethers in Water
    Lindstedt, Erik
    Ghosh, Raju
    Olofsson, Berit
    ORGANIC LETTERS, 2013, 15 (23) : 6070 - 6073
  • [35] Convenient, functional group-tolerant, transition metal-free synthesis of aryl and heteroaryl trifluoromethyl ketones with the use of methyl trifluoroacetate
    Funabiki, Kazumasa
    Hayakawa, Ayaka
    Inuzuka, Toshiyasu
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (06) : 913 - 918
  • [36] Efficient Synthesis of Diarylmethanamines via Transition-Metal-Free Double-Insertive Coupling of Isocyanides with Arylboronic Acids
    Zheng, Long
    Wang, Peng
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2021, 41 (03) : 1272 - 1273
  • [37] Transition metal free one pot synthesis of aryl carboxylic acids via dehomologative oxidation of styrenes
    Patil, Bhausaheb N.
    Sathe, Pratima A.
    Parade, Babasao S.
    Vadagaonkar, Kamlesh S.
    Chaskar, Atul C.
    TETRAHEDRON LETTERS, 2018, 59 (49) : 4340 - 4343
  • [38] Transition-Metal-Free Synthesis of N-Aryl Hydroxamic Acids via Insertion of Arynes
    Zhang, Lanlan
    Geng, Yu
    Jin, Zhong
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (09): : 3542 - 3552
  • [39] Metal-free synthesis of biarenes via photoextrusion in di(tri)aryl phosphates
    Qrareya, Hisham
    Meazza, Lorenzo
    Protti, Stefano
    Fagnoni, Maurizio
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2020, 16 : 3008 - 3014
  • [40] Transition Metal-free Selenium-mediated Aryl Amines via Reduction of Nitroarenes
    Capperucci, Antonella
    Clemente, Martina
    Cenni, Alessio
    Tanini, Damiano
    CHEMSUSCHEM, 2023, 16 (15)