1,6-Conjugate addition of in situ generated aryldiazenes to p-quinone methides.
Org Biomol Chem
; 22(27): 5636-5645, 2024 Jul 10.
Article
em En
| MEDLINE
| ID: mdl-38912576
ABSTRACT
Herein we report a transition-metal free, base-mediated 1,6-conjugate addition of aryldiazenes to para-quinone methides (p-QMs). Arylhydrazines were used for the in situ generation of aryldiazenes using a base-mediated protocol in the presence of air as the oxidant. The 1,6-conjugate addition of aryldiazenes to para-quinone methides via a radical mechanism is followed by an oxidative rearrangement to furnish the desired product, arylhydrazones. Interestingly, our synthetic protocol results in the formation of an aryldiazene radical, which undergoes 1,6-conjugate addition with p-QMs to furnish the arylhydrazones.
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MEDLINE
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En
Ano de publicação:
2024
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Article