Platform for Ring-Fluorinated Benzoheterole Derivatives: Palladium-Catalyzed Regioselective 1,1-Difluoroallylation and Heck Cyclization

被引：37
|
作者：
Fujita, Takeshi [1 ]
Sugiyama, Kazuki [1 ]
Sanada, Shohei [1 ]
Ichitsuka, Tomohiro [1 ]
Ichikawa, Junji [1 ]
机构：
[1] Univ Tsukuba, Fac Pure & Appl Sci, Div Chem, Tsukuba, Ibaraki 3058571, Japan
来源：
ORGANIC LETTERS | 2016年 / 18卷 / 02期
关键词：
NUCLEOPHILIC-SUBSTITUTION; ALLYLIC DIFLUORIDES; BOND; HETEROCYCLES; ACTIVATION; ALCOHOLS; ACCESS;
D O I：
10.1021/acs.orglett.5b03390
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The synthesis of difluoromethylene-containing heterocycles was achieved via the palladium-catalyzed 1,1-difluoroallylation of heteronucleophiles followed by intramolecular Heck reaction. The allylic substitution of 3-bromo-3,3-difluoropropene was regioselectively accomplished by heteronucleophiles without rearrangement to give the corresponding 1,1-difluoroallylated compounds whose Heck cyclization proceeded in a 5-exo manner to afford ring-difluorinated indolines and dihydrobenzofurans. Their defluorinative allylic substitution further provided 2-fluoroindoles and 2-fluorobenzofurans.
引用
收藏
页码：248 / 251
页数：4
相关论文
共 12 条
  • [1] Palladium-Catalyzed Regioselective Heck-Suzuki-Miyaura Cascade Cyclization for the Synthesis of Trisubstituted Arylideneisoquinolinones
    Asgari, M. S.
    Mirzazadeh, R.
    Larijani, B.
    Ranjbar, P. Rashidi
    Rahimi, R.
    Mahdavi, M.
    SYNLETT, 2019, 30 (09) : 1073 - 1076
  • [2] Regioselective synthesis of oxazole derivatives via palladium-catalyzed and copper-mediated cascade oxidative cyclization
    Zheng, Jia
    Zhang, Min
    Huang, Liangbin
    Hu, Xiaohan
    Wu, Wanqing
    Huang, Huawen
    Jiang, Huangfeng
    CHEMICAL COMMUNICATIONS, 2014, 50 (27) : 3609 - 3611
  • [3] Palladium-Catalyzed Regioselective 5-exo-O-Cyclization/Oxidative Heck Cascades from o-Alkynylbenzamides and Electron-Deficient Alkenes
    Madich, Youssef
    Alvarez, Rosana
    Aurrecoechea, Jose M.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (28) : 6263 - 6271
  • [4] Palladium-Catalyzed Carbo-Aminative Cyclization of 1,6-Enynes: Access to Napthyridinone Derivatives
    Babu, Undamatla Suri
    Singam, Maneesh Kumar Reddy
    Kumar, Muniganti Naveen
    Nanubolu, Jagadeesh Babu
    Reddy, Maddi Sridhar
    ORGANIC LETTERS, 2022, 24 (08) : 1598 - 1603
  • [5] Palladium-catalyzed radical cascade cyanoalkylsulfonylation/cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with cyclobutanone oxime esters and DABSO
    Zhou, Nengneng
    Xu, Qiankun
    Xia, Ziqin
    Kuang, Kaimo
    Wu, Sixin
    Li, Wenping
    Zhang, Man
    CHEMICAL COMMUNICATIONS, 2022, 58 (14) : 2335 - 2338
  • [6] Facile Preparation of Indoles and 1,2-Benzothiazine 1,1-Dioxides: Nucleophilic Addition of Sulfonamides to Bromoacetylenes and Subsequent Palladium-Catalyzed Cyclization
    Yamagishi, Masahito
    Nishigai, Ken
    Ishii, Azusa
    Hata, Takeshi
    Urabe, Hirokazu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (26) : 6471 - 6474
  • [7] The nucleophilic 5-endo-trig cyclization of 1,1-difluoro-l-alkenes:: Ring-fluorinated hetero- and carbocycle synthesis and remarkable effect of the vinylic fluorines on the disfavored process
    Ichikawa, J
    Wada, Y
    Fujiwara, M
    Sakoda, K
    SYNTHESIS-STUTTGART, 2002, (13): : 1917 - 1936
  • [8] Synthesis of 1-Difluoroalkylated Isoquinolines via Palladium-Catalyzed Radical Cascade Difluoroalkylation-Cyclization of Vinyl Isocyanides with Bromodifluoroacetic Derivatives
    Liu, Yingle
    Zhang, Ke
    Jiang, Weidong
    Yang, Yi
    Jiang, Yan
    Liu, Xiaoqiang
    Xie, Ying
    Wu, Jincai
    Cai, Junjie
    Xu, Xiu-Hua
    CHEMISTRY-AN ASIAN JOURNAL, 2017, 12 (05) : 568 - 576
  • [9] Dibenzo[ b , e ]azepin-6-ones and Seven-Membered Sultam Derivatives: Convenient Synthesis via Palladium-Catalyzed Regioselective Intra-molecular Heck Reaction and Application towards Drug-Like Small Molecules
    Das, Arijit
    Maiti, Arup
    Kundu, Mrinalkanti
    Roy, Kuldeep K.
    Ansary, Inul
    SYNTHESIS-STUTTGART, 2019, 51 (17): : 3231 - 3240
  • [10] Palladium-catalyzed direct C-H arylation of 3-aryl-2H-benzo[1,2,4]thiadiazine 1,1-dioxides: an efficient strategy to the synthesis of benzothiadiazine-1,1-dioxide derivatives
    Wang, Dongyin
    Liu, Wei
    Yi, Fei
    Zhao, Yongli
    Chen, Junmin
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (06) : 1921 - 1924
12