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

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
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Publikationsverlauf

Received: 26. März 2014

Accepted after revision: 24. Juli 2014

Publikationsdatum:
03. September 2014 (online)


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

 
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