A new domino Heck-isomerization/Saegusa/Heck reaction of propenol with aryl iodides has been developed for the synthesis of 3,3-diaryl propenals by triple transition-metal catalysis. Moreover, we also developed the domino Heck-isomerization/Heck-type reaction of propenol with aryl iodides for the synthesis of 1,3-diaryl propanones by double transition-metal catalysis and the mediation of secondary amine or triple transition metal catalysis and aminocatalysis.
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http://dx.doi.org/10.1021/acs.joc.5b01650 | DOI Listing |
RSC Adv
October 2023
Department of Medicinal and Applied Chemistry, Kaohsiung Medical University Kaohsiung 807 Taiwan
In this study, the present research describes a high-yield method for the synthesis of sulfonyl 2-aryl-5-methylenetetrahydropyrans by one-pot straightforward DABCO-promoted intramolecular Michael addition of β-sulfonyl styrene with 2-chloromethyl-1-propenol followed by intramolecular alkylation. This Baylis-Hillman-type pathway provides a highly effective stereoselective annulation by forming one carbon-oxygen bond and one carbon-carbon bond.
View Article and Find Full Text PDFJ Org Chem
September 2015
Department of Chemistry, Zhejiang University, Hangzhou 310028, China.
A new domino Heck-isomerization/Saegusa/Heck reaction of propenol with aryl iodides has been developed for the synthesis of 3,3-diaryl propenals by triple transition-metal catalysis. Moreover, we also developed the domino Heck-isomerization/Heck-type reaction of propenol with aryl iodides for the synthesis of 1,3-diaryl propanones by double transition-metal catalysis and the mediation of secondary amine or triple transition metal catalysis and aminocatalysis.
View Article and Find Full Text PDFChem Commun (Camb)
April 2011
Key Laboratory of Mesoscopic Chemistry of MOE, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, P. R. China.
An unprecedented cascade Heck-Aldol-Heck reaction was developed to form two C-C single bonds and one C=C double bond in one process by a combination of palladium(0) catalysis and aminocatalysis. Various aryl iodides could perform the cascade reaction with readily available propenol and formaldehyde to afford novel (E)-trisubstituted alkenes in 66-81% yields.
View Article and Find Full Text PDFJ Org Chem
November 2005
Dipartimento di Chimica Organica, Università di Pavia, V.le Taramelli 10, 27100 Pavia, Italy.
[Reaction: see text]. RB3LYP calculations, reported here, indicate that peroxy acid s-cis conformer is more stable than its s-trans counterpart, in agreement with experimental data. Difference in stability is the highest in the gas phase, but it falls considerably on going from the gas phase to moderately polar solvent.
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