Tunable Construction of Multisubstituted 1,3-Dienes and Allenes via a 1,4-Palladium Migration/Carbene Insertion Cascade

Jie Lin, Zilong Huang, Juan Ma, Bao Hua Xu, Yong Gui Zhou*, Zhengkun Yu*

*Corresponding author for this work

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Abstract

Efficient palladium-catalyzed vinylic C-H alkenylation and allenylation of gem-disubstituted ethylenes with N-tosylhydrazones of aryl alkyl and diaryl ketones were achieved to access trisubstituted 1,3-dienes and tetrasubstituted allenes, respectively. An aryl to vinyl 1,4-palladium migration/carbene insertion/β-hydride elimination sequence proceeded to switch the chemo- and regioselectivities to give structurally diverse products. Use of 2-FC6H4OH additive enables enhancement of the reaction efficiency through accelerating the key 1,4-palladium migration process.

Original languageEnglish
Pages (from-to)12019-12035
Number of pages17
JournalJournal of Organic Chemistry
Volume87
Issue number18
DOIs
Publication statusPublished - 16 Sept 2022
Externally publishedYes

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Lin, J., Huang, Z., Ma, J., Xu, B. H., Zhou, Y. G., & Yu, Z. (2022). Tunable Construction of Multisubstituted 1,3-Dienes and Allenes via a 1,4-Palladium Migration/Carbene Insertion Cascade. Journal of Organic Chemistry, 87(18), 12019-12035. https://doi.org/10.1021/acs.joc.2c01019