Palladium-Catalyzed Selective Syntheses of 2,3-Allenyl Amines via Double Functionalization Coupling of 2-Alkynyl-1,4-diol Dicarbonates
Zhengnan Zhou
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorCan Li
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorCorresponding Author
Shengming Ma
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 China
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433 China
E-mail: [email protected]Search for more papers by this authorZhengnan Zhou
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorCan Li
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 China
University of Chinese Academy of Sciences, Beijing, 100049 China
Search for more papers by this authorCorresponding Author
Shengming Ma
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai, 200032 China
Research Center for Molecular Recognition and Synthesis, Department of Chemistry, Fudan University, 220 Handan Lu, Shanghai, 200433 China
E-mail: [email protected]Search for more papers by this authorComprehensive Summary
2,3-Allenyl amines have shown wide applicability in biomedical and synthetic applications. Due to their enormous potential for applications, researchers have been dedicated to the development of methods for synthesizing 2,3-allenyl amines. Herein, a palladium-catalyzed three-component reaction of 2-alkynyl-1,4-diol dicarbonates, organoboronic acids, and nitrogen nucleophiles forming 2,3-allenyl amines with excellent regio- and chemo-selectivity has been developed. Substrate compatibility and synthetic applications have been demonstrated. Control experiments supported a mechanism involving 1,2,3-triene-Pd species and methylene-π-allyl palladium species.
Supporting Information
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