Stereoselective Synthesis of Tetrasubstituted Olefins via Visible-Light-Promoted Iodine-Mediated Homo-Coupling of Diazo.
J Org Chem
; 87(17): 11826-11837, 2022 Sep 02.
Article
em En
| MEDLINE
| ID: mdl-36001822
ABSTRACT
A visible-light-promoted iodine-mediated homo-coupling of diazo was first described. A series of tetrasubstituted olefins were synthesized in high yields and with low to high Z-selectivities from phenyldiazoacetates. For 3-diazooxindoles, isoindigo derivatives were provided in moderate to high yields and with excellent E-selectivities. Experimental results showed that the reaction proceeded through a diiodo intermediate. The synthetic usefulness of this reaction was illustrated by the synthesis of maleimide derivatives and dispiro epoxy.
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MEDLINE
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2022
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Article