Ligand-Free Iron-Catalyzed Carbon (sp2)-Carbon (sp2) Oxidative Homo-Coupling of Alkenyllithiums

Zhuliang Zhong; Zhi-Yong Wang; Shao-Fei Ni; Li Dang; Hung Kay Lee; Xiao-Shui Peng; Henry N C Wong

doi:10.1021/acs.orglett.8b03893

Ligand-Free Iron-Catalyzed Carbon (sp²)-Carbon (sp²) Oxidative Homo-Coupling of Alkenyllithiums

Org Lett. 2019 Feb 1;21(3):700-704. doi: 10.1021/acs.orglett.8b03893. Epub 2019 Jan 24.

Authors

Zhuliang Zhong¹, Zhi-Yong Wang¹, Shao-Fei Ni², Li Dang², Hung Kay Lee¹, Xiao-Shui Peng^{1

3}, Henry N C Wong^{1

3}

Affiliations

¹ Department of Chemistry and State Key Laboratory of Synthetic Chemistry , The Chinese University of Hong Kong , Shatin , New Territories, Hong Kong SAR, China.
² Department of Chemistry and Key Laboratory for Preparation and Application of Ordered Structural Materials of Guangdong Province , Shantou University , Shantou , Guangdong 515063 , P. R. China.
³ Shenzhen Center of Novel Functional Molecules, Shenzhen Research Institute , The Chinese University of Hong Kong , No. 10, Second Yuexing Road , Shenzhen 518507 , P. R. China.

PMID: 30675791
DOI: 10.1021/acs.orglett.8b03893

Abstract

A new strategy was developed for the efficient synthesis of di-, tetra-, and hexa-substituted 1,3-butadienes. This one-pot procedure involves lithium-iodine exchange to generate the corresponding vinyllithium intermediates. A subsequent iron-catalyzed ligand-free oxidative homo-coupling eventually led to the formation of 1,3-butadienes in acceptable to excellent isolated yields.

Publication types

Research Support, Non-U.S. Gov't