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Allene-ZhangG190604.pdf (861.98 kB)

Synthesis of Tetrasubstituted Allenes via Palladium-Catalyzed Cross-Coupling of Vinyl Bromides with Diazo Compounds

submitted on 04.12.2019, 13:11 and posted on 12.12.2019, 08:56 by Ge Zhang, Ze-Jian Xue, Fang Zhang, Shu-Sheng Zhang, Meng-Yao Li, Bin-Bin Zhu, Chen-Guo Feng, Guo-Qiang Lin
A highly efficient palladium-catalyzed cross-coupling of 2,2-diarylvinyl bromides with diazo compounds was developed, providing a convenient approach for the synthesis of tetrasubsti-tuted allenes. Both aryl diazo carbonyl compounds and N-tosylhydrazones are competent carbene precursors in this reaction. An unprecedented hydrogen elimination of the π-allyl palladium intermediate is proposed to be the key step.


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Shanghai Institute of Organic Chemistry



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Declaration of Conflict of Interest

The authors declare no competing financial interests.