Metal-Free Cyclopropanol Ring-Opening C(sp3)-C(sp2) Cross-Couplings with Aryl Sulfoxides

被引：26
|
作者：
Chen, Dengfeng [1 ]
Fu, Yuanyuan [1 ]
Cao, Xiaoji [2 ]
Luo, Jinyue [1 ]
Wang, Fei [1 ]
Huang, Shenlin [1 ]
机构：
[1] Nanjing Forestry Univ, Coll Chem Engn,Jiangsu Prov Key Lab Chem & Utiliz, Jiangsu Coinnovat Ctr Efficient Proc & Utilizat F, Jiangsu Key Lab Biomass Based Green Fuels & Chem, Nanjing 210037, Jiangsu, Peoples R China
[2] Zhejiang Univ Technol, Coll Chem Engn, 18 Chaowang Rd, Hangzhou 310014, Zhejiang, Peoples R China
来源：
ORGANIC LETTERS | 2019年 / 21卷 / 14期
关键词：
PUMMERER REACTION CHEMISTRY; C-METHYLATED DIHYDROCHALCONES; NUCLEOPHILIC ORTHO-ALLYLATION; BOND-FORMING REACTIONS; DIRECT BETA-ARYLATION; OXIDATIVE CYCLIZATION; INTERRUPTED PUMMERER; ALPHA-ARYLATION; KETONES; PALLADIUM;
D O I：
10.1021/acs.orglett.9b01908
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A metal-free method for formal beta-arylation/heteroarylation of ketones through efficient cyclopropanol ring-opening cross-couplings with aryl sulfoxides at room temperature has been developed. This protocol shows a broad substrate scope and promising scalability. In addition, the utility of the beta-arylated ketones is further demonstrated through a variety of postcoupling transformations and synthetic applications.
引用
收藏
页码：5600 / 5605
页数：6
相关论文
共 50 条
  • [31] Functionalization of C(sp3)-H Bonds Adjacent to Oxygen of Alcohols under Metal-free Conditions
    Dong, Dao-Qing
    Hao, Shuang-Hong
    Wang, Zu-Li
    MINI-REVIEWS IN ORGANIC CHEMISTRY, 2017, 14 (02) : 130 - 135
  • [32] Metal-free C(sp3)-H Bromination: Synthesis of Phenacyl bromide and Benzyl bromide derivatives
    Sourav Mal
    Satinath Sarkar
    Manoranjan Jana
    Journal of Chemical Sciences, 134
  • [33] Metal-free C(sp3)-H Bromination: Synthesis of Phenacyl bromide and Benzyl bromide derivatives
    Mal, Sourav
    Sarkar, Satinath
    Jana, Manoranjan
    JOURNAL OF CHEMICAL SCIENCES, 2022, 134 (04)
  • [34] Cross-Coupling Reactions between C(sp2)-H and C(sp3)-H Bonds via Sequential Dehydrogenation and C-H Insertion
    Kuninobu, Yoichiro
    Asanoma, Daisuke
    Takai, Kazuhiko
    SYNLETT, 2010, (19) : 2883 - 2886
  • [35] Pyridine-enabled copper-promoted cross dehydrogenative coupling of C(sp2)-H and unactivated C(sp3)-H bonds
    Wu, Xuesong
    Zhao, Yan
    Ge, Haibo
    CHEMICAL SCIENCE, 2015, 6 (10) : 5978 - 5983
  • [36] Nickel-catalyzed directed sulfenylation of sp2 and sp3 C-H bonds
    Ye, Xiaohan
    Petersen, Jeffrey L.
    Shi, Xiaodong
    CHEMICAL COMMUNICATIONS, 2015, 51 (37) : 7863 - 7866
  • [37] Stereospecific Palladium-Catalyzed Decarboxylative C(sp3)-C(sp2) Coupling of 2,5-Cyclohexadiene-1-carboxylic Acid Derivatives with Aryl Iodides
    Chou, Chih-Ming
    Chatterjee, Indranil
    Studer, Armido
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (37) : 8614 - 8617
  • [38] MnI/AgI Relay Catalysis: Traceless Diazo-Assisted C(sp2)-H/C(sp3)-H Coupling to β-(Hetero)Aryl/Alkenyl Ketones
    Lu, Qingquan
    Mondal, Shobhan
    Cembellin, Sara
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (33) : 10732 - 10736
  • [39] Catalytic C(sp2)-C(sp3) Cross-Electrophile Coupling in the PtII-NaI-С2Н3I-СН3I-Acetone System
    Krasnyakova, T. V.
    Nikitenko, D. V.
    Mitchenko, S. A.
    KINETICS AND CATALYSIS, 2024, 65 (01) : 30 - 39
  • [40] Role of TMEDA in Iron-Catalyzed C(sp2)-C(sp3) Cross-Coupling Reactions: A Mechanistic Study Using DFT Calculations
    Wan, Xin
    Zhao, Tianchu
    Ren, Qinghua
    Zhou, Gangchang
    ORGANOMETALLICS, 2024, 43 (04) : 449 - 456
12345