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

Jie LinZilong HuangJuan MaBao-Hua XuYong-Gui ZhouZheng-Kun Yu
Published in: The Journal of organic chemistry (2022)
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-FC 6 H 4 OH additive enables enhancement of the reaction efficiency through accelerating the key 1,4-palladium migration process.
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