Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 87, Issue 18, Pages 12019-12035Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.2c01019
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Funding
- National Natural Science Foundation of China [22171261, 21871253]
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Efficient palladium-catalyzed reactions were utilized to synthesize diverse compounds, including trisubstituted 1,3-dienes and tetrasubstituted allenes. The chemo- and regioselectivities were controlled to obtain structurally diverse products.
Efficient palladium-catalyzed vinylic C-H alkenylation and allenylation of gem-disubstituted ethylenes with N-tosylliydrazones 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/beta-hydride elimination sequence proceeded to switch the chemo- and regioselectivities to give structurally diverse products. Use of 2-FC6H2OH additive enables enhancement of the reaction efficiency through accelerating the key 1,4-palladium migration process.
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