Synthesis 2014; 46(23): 3191-3198
DOI: 10.1055/s-0034-1378652
paper
© Georg Thieme Verlag Stuttgart · New York

Transition-Metal-Catalyzed Synthesis of 1,3-Diynes and Ynamides from 2-Bromo-1-iodoalkenes

Authors

  • Jun Xue

    Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, P. R. of China   Fax: +86(793)8393670   Email: chenzwang@gnnu.cn
  • Miao-Ting Luo

    Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, P. R. of China   Fax: +86(793)8393670   Email: chenzwang@gnnu.cn
  • Yue-Lu Wen

    Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, P. R. of China   Fax: +86(793)8393670   Email: chenzwang@gnnu.cn
  • Min Ye

    Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, P. R. of China   Fax: +86(793)8393670   Email: chenzwang@gnnu.cn
  • Liang-Xian Liu

    Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, P. R. of China   Fax: +86(793)8393670   Email: chenzwang@gnnu.cn
  • Zheng-Wang Chen*

    Key Laboratory of Organo-Pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, P. R. of China   Fax: +86(793)8393670   Email: chenzwang@gnnu.cn
Further Information

Publication History

Received: 26 March 2014

Accepted after revision: 24 July 2014

Publication Date:
03 September 2014 (online)


Graphical Abstract

Abstract

Diynes and ynamides are important products in chemical synthesis. An efficient palladium-catalyzed homocoupling reaction of 2-bromo-1-iodoalkenes to give 1,3-diynes has been developed. The reactions are conducted under convenient conditions and provide products in moderate to excellent yields. Moreover, ynamides were synthesized from 2-bromo-1-iodoalkenes and carbamates, and it is noteworthy that this reaction is catalyzed by nanoparticulate copper(I) oxide to give ynamides in high yields.

Supporting Information