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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
Preprints are manuscripts made publicly available before they have been submitted for formal peer review and publication. They might contain new research findings or data. Preprints can be a draft or final version of an author's research but must not have been accepted for publication at the time of submission.
submitted on 04.12.2019, 13:11 and posted on 12.12.2019, 08:56by 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.