Journal
SYNTHETIC COMMUNICATIONS
Volume 50, Issue 4, Pages 526-538Publisher
TAYLOR & FRANCIS INC
DOI: 10.1080/00397911.2019.1704786
Keywords
Diazonium salt; iron powder; Meerwein arylation; radical reaction; reducing agent; tin; tin chloride
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Funding
- French government - French Embassy in Egypt (Institut Francais d'Egypte)
- Egyptian government - French Embassy in Egypt (Institut Francais d'Egypte)
- Science and Technology Development Fund (STDF)
- Plant Advanced Technologies (PAT)
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Simple and rapid route for Meerwein arylation reaction using iron powder or a mixture of tin/tin chloride has been developed. In the presence of iron powder, different aryl diazonium salts reacted with methyl vinyl ketone, acrylates, and isopropenyl acetate. Production of oximes was detected as the main product with acrylates or in a mixture with beta-aryl methyl ketones in the case of methyl vinyl ketone. The in situ produced HNO2 from an excess of NaNO2/HCl was trapped by alkyl aryl radical to form oximes in the E configuration form. The presence of tin/tin chloride mixture in the reaction of the aryl diazonium salts with methyl vinyl ketone produced Michael products along with beta-aryl methyl ketones. The predicted alpha-aryl methyl ketones from the reaction of isopropenyl acetate with the diazotized anilines were obtained using iron or tin/tin chloride mixture.
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