Palladium-Catalyzed Regioselective C-Arylation and C,N-Diarylation of N-Aryl-2,3-dihydrophthalazine-1,4-diones Using Diaryliodonium Salts

被引:3
|
作者
Naharwal, Sushma [1 ]
Kharat, Narendra Dinkar [1 ]
Mahesha, Chikkagundagal K. [1 ]
Bajaj, Kiran [2 ]
Sakhuja, Rajeev [1 ,2 ]
机构
[1] Birla Inst Technol & Sci, Dept Chem, Pilani 333031, Rajasthan, India
[2] Amity Univ, Amity Inst Appl Sci, Dept Chem, Noida, Uttar Pradesh, India
来源
SYNTHESIS-STUTTGART | 2023年 / 55卷 / 21期
关键词
arylation; biaryls; catalysis; palladium; transition metals; BIOLOGICAL EVALUATION; H ARYLATION; DESIGN; INDOLES; PHTHALAZINE; EFFICIENT;
D O I
10.1055/a-2048-8030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Regioselective C-arylation and C,N-diarylation in 2-aryl-2,3dihydrophthalazine-1,4-diones has been successfully accomplished with diaryliodonium salts under base-mediated slightly modified Pd catalyzed conditions. These ligand-driven transformations provided a variety of diversely decorated bi(hetero)aryls in good-to-excellent yields, while N-arylated product could be obtained under similar Pd -catalyzed conditions in the absence of a ligand.
引用
收藏
页码:3515 / 3525
页数:11
相关论文
共 24 条
  • [1] Ruthenium-catalyzed (spiro)annulation of N-aryl-2,3-dihydrophthalazine-1,4-diones with quinones to access pentacyclic spiro-indazolones and fused-cinnolines
    Naharwal, Sushma
    Karishma, Pidiyara
    Mahesha, Chikkagundagal K.
    Bajaj, Kiran
    Mandal, Sanjay K.
    Sakhuja, Rajeev
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (23) : 4753 - 4764
  • [2] Palladium-Catalyzed Regioselective C-H Arylation of Quinoline-N-Oxides at C-8 Position using Diaryliodonium Salts
    Sharma, Shivani
    Kumar, Sehdev
    Sharma, Anuj
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2020, 9 (04) : 660 - 667
  • [3] Rhodium-Catalyzed Spirocyclization of Maleimide with N-Aryl-2,3-dihydrophthalazine-1,4-dione to Access Pentacyclic Spiro-Succinimides
    Karishma, Pidiyara
    Mandal, Sanjay K.
    Sakhuja, Rajeev
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 10 (10) : 2580 - 2590
  • [4] Palladium-Catalyzed Regioselective C-5 Arylation of 1,2,3-Triazoles with Diaryliodonium Salts
    Gang, Fangli
    Che, Yang
    Du, Zhengyin
    Feng, Hua
    Fu, Ying
    SYNLETT, 2017, 28 (13) : 1624 - 1629
  • [5] Transition-Metal-Free N-Arylation of Carbazoles and C-Arylation of Tetrahydrocarbazoles by using Diaryliodonium Salts
    Guo, Fenglou
    Wang, Limin
    Wang, Peiqi
    Yu, Jianjun
    Han, Jianwei
    ASIAN JOURNAL OF ORGANIC CHEMISTRY, 2012, 1 (03) : 218 - 221
  • [6] Palladium-Catalyzed Regioselective C-2 Arylation of Benzofurans with N-Acyl Arylhydrazines
    Cao, Jun
    Chen, Zi-Li
    Li, Shu-Min
    Zhu, Gao-Feng
    Yang, Yuan-Yong
    Wang, Cong
    Chen, Wen-Zhang
    Wang, Jian-Ta
    Zhang, Ji-Quan
    Tang, Lei
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (22) : 2774 - 2779
  • [7] Domino N-/C-Arylation via In Situ Generation of a Directing Group: Atom-Efficient Arylation Using Diaryliodonium Salts
    Teskey, Christopher J.
    Sohel, Shariar M. A.
    Bunting, Danielle L.
    Modha, Sachin G.
    Greaney, Michael F.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (19) : 5263 - 5266
  • [8] Expeditious synthesis of C2- or N4-aryl-1,4-benzothiazin-3-one via orthogonal Pd-catalyzed C-arylation and Cu-catalyzed N-arylation
    Huang, Wei-Sheng
    Xu, Rongsong
    Dodd, Rory
    Shakespeare, William C.
    TETRAHEDRON LETTERS, 2014, 55 (02) : 441 - 444
  • [9] Palladium-catalyzed direct C-H arylation of pyridine N-oxides with potassium aryl- and heteroaryltrifluoroborates
    Li, Mengli
    Li, Xing
    Chang, Honghong
    Gao, Wenchao
    Wei, Wenlong
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (08) : 2421 - 2426
  • [10] Palladium-Catalyzed Direct C3-Selective Arylation of N-Unsubstituted Indoles with Aryl Chlorides and Triflates
    Yamaguchi, Miyuki
    Suzuki, Kohei
    Sato, Yusuke
    Manabe, Kei
    ORGANIC LETTERS, 2017, 19 (19) : 5388 - 5391