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Generation of Allenic/Propargylic Zirconium Complexes and Subsequent Cross-Coupling Reactions: A Facile Synthesis of Multisubstituted Allenes

Hao Zhang, Xiaoping Fu, Jingjin Chen, Erjuan Wang, Yuanhong Liu* and Yuxue Li

*State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China, Email: yhliumail.sioc.ac.cn

H. Zhang, X. Fu, J. Chen, E. Wang, Y. Liu, X. Li, J. Org. Chem., 2009, 74, 9351-9358.

DOI: 10.1021/jo9020419 (free Supporting Information)


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Abstract

The β-alkoxide elimination reaction of aryl- or alkyl-subsituted propargylic ethers with Negishi reagent leads to allenes after hydrolysis, whereas TMS-substituted substrates afford alkynes. Subsequent coupling reactions of the zirconium intermediates with aryl iodides in the presence of Pd(PPh3)4/CuCl provide a straightforward route for the synthesis of multisubstituted allenes.

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Key Words

Allenes (Elimination, Coupling)


ID: J42-Y2009-3610