Palladium-Mediated Tandem Isomerization-Methylenation of Allyl Alcohols: One-Pot Synthesis of 1,5-Diketones.

Shaikh Samser, Omkar Mohapatra, Priyabrata Biswal, Krishnan Venkatasubbaiah

The Journal of organic chemistry 2021 Oct 01

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A novel methodology for the synthesis of 1,5-diketones through a one-pot isomerization-methylenation of a variety of allylic alcohols has been established for the first time. This methodology utilizes commercially available palladium acetate and easily accessible BINOL phosphoric acid. Both isomerization of allylic alcohol and oxidation of methanol occurred through a single catalyst. The practical utility of the methodology has been shown by synthesizing substituted pyridines via sequential addition. Mechanistic investigation reveals the isomerization of allylic alcohols to the corresponding ketone, which ultimately undergoes methylenation, leading to 1,5-diketones, having H2 and H2O as the only byproduct.

Citation

Shaikh Samser, Omkar Mohapatra, Priyabrata Biswal, Krishnan Venkatasubbaiah. Palladium-Mediated Tandem Isomerization-Methylenation of Allyl Alcohols: One-Pot Synthesis of 1,5-Diketones. The Journal of organic chemistry. 2021 Oct 01;86(19):13744-13753