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 language | English |
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Pages (from-to) | 12019-12035 |
Number of pages | 17 |
Journal | Journal of Organic Chemistry |
Volume | 87 |
Issue number | 18 |
DOIs | |
Publication status | Published - 16 Sept 2022 |
Externally published | Yes |
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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