One-pot synthesis of diarylalkynes using palladium-catalyzed Sonogashira reaction and decarboxylative coupling of sp carbon and sp2 carbon

被引:268
|
作者
Moon, Jeongju [1 ]
Jeong, Miso [1 ]
Nam, Hyungoog [1 ]
Ju, Jinhun [1 ]
Moon, Joong Ho [2 ]
Jung, Hyun Min [3 ]
Lee, Sunwoo [1 ]
机构
[1] Chonnam Natl Univ, Dept Chem, Kwangju 500757, South Korea
[2] ICx Nomad Inc, Cambridge, MA 02142 USA
[3] Korea Res Inst Chem Technol, Adv Mat Div, Taejon 305600, South Korea
关键词
D O I
10.1021/ol703130y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Decarboxylative coupling of sp-sp(2) carbons is possible by palladium catalyst. Employing propiolic acid (1) as a difunctional alkyne, and using the consecutive reactions of the Sonogashira reaction and the decarboxylative coupling, unsymmetrically substituted diaryl alkynes were obtained in moderate to good yield.
引用
收藏
页码:945 / 948
页数:4
相关论文
共 50 条
  • [41] One-Pot Palladium(II)-Catalyzed Synthesis of Fluorenones via Decarboxylative Cyclization
    Cai, Zhiqiang
    Hou, Xu
    Hou, Ling
    Hu, Zhiquan
    Zhang, Bo
    Jin, Zhengsheng
    SYNLETT, 2016, 27 (03) : 395 - 398
  • [42] One-pot palladium-catalyzed cross-coupling reaction of aryl iodides with stannylarsanes and stannylstibanes
    Bonaterra, M
    Martín, SE
    Rossi, RA
    ORGANIC LETTERS, 2003, 5 (15) : 2731 - 2734
  • [43] One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
    Jong, Howard
    Eey, Stanley T. -C.
    Lim, Yee Hwee
    Pandey, Sangeeta
    Iqbal, Nurul Azmah Bte
    Yong, Fui Fong
    Robins, Edward G.
    Johannes, Charles W.
    ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (04) : 616 - 622
  • [44] One-pot synthesis of recyclable palladium catalysts for hydrogenations and carbon-carbon coupling reactions
    Kim, N
    Kwon, MS
    Park, CM
    Park, J
    TETRAHEDRON LETTERS, 2004, 45 (38) : 7057 - 7059
  • [45] Efficient palladium-catalyzed C(sp2)-H activation towards the synthesis of fluorenes
    Song, Juan
    Li, Yali
    Sun, Wei
    Yi, Chenglong
    Wu, Hao
    Wang, Haotian
    Ding, Keran
    Xiao, Kang
    Liu, Chao
    NEW JOURNAL OF CHEMISTRY, 2016, 40 (11) : 9030 - 9033
  • [46] Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from sp2-carbon
    Ge Zhang
    Yi-Kang Song
    Fang Zhang
    Ze-Jian Xue
    Meng-Yao Li
    Gui-Shan Zhang
    Bin-Bin Zhu
    Jing Wei
    Chunsen Li
    Chen-Guo Feng
    Guo-Qiang Lin
    Nature Communications, 12
  • [47] Palladium-catalyzed allene synthesis enabled by β-hydrogen elimination from sp2-carbon
    Zhang, Ge
    Song, Yi-Kang
    Zhang, Fang
    Xue, Ze-Jian
    Li, Meng-Yao
    Zhang, Gui-Shan
    Zhu, Bin-Bin
    Wei, Jing
    Li, Chunsen
    Feng, Chen-Guo
    Lin, Guo-Qiang
    NATURE COMMUNICATIONS, 2021, 12 (01)
  • [48] Palladium-Catalyzed C(sp2)-N Bond Cross-Coupling with Triaryl Phosphates
    Chen, Zicong
    Chen, Xiangmeng
    So, Chau Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (10): : 6366 - 6376
  • [49] Palladium-Catalyzed Carbonylative Sonogashira Coupling of Aryl Bromides Using Near Stoichiometric Carbon Monoxide
    Neumann, Karoline T.
    Laursen, Simon R.
    Lindhardt, Anders T.
    Bang-Andersen, Benny
    Skrydstrup, Troels
    ORGANIC LETTERS, 2014, 16 (08) : 2216 - 2219
  • [50] Palladium-Catalyzed sp2-sp3 Coupling of Chloromethylarenes with Allyltrimethoxysilane: Synthesis of Allyl Arenes
    Zhang, Sheng
    Cai, Jinfang
    Yamamoto, Yoshinori
    Bao, Ming
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (11): : 5974 - 5980