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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

preprint
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.

History

Email Address of Submitting Author

fengcg@sioc.ac.cn

Institution

Shanghai Institute of Organic Chemistry

Country

China

ORCID For Submitting Author

0000-0001-9899-9489

Declaration of Conflict of Interest

The authors declare no competing financial interests.

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