Dearomative (3+2) Cycloadditions between Indoles and Vinyldiazo Species Enabled by a Red-Shifted Chromium
Bradley K Gall1, Avery K Smith1, Eric M Ferreira1
1Department of Chemistry, University of Georgia, Athens, GA 30602, USA.
Abstract:
A direct dearomative photocatalyzed (3+2) cycloaddition between indoles and vinyldiazo reagents is described. The transformation is enabled by the development of a novel oxidizing CrIII photocatalyst, its specific reactivity attributed to increased absorptive properties over earlier Cr analogs and greater stability than Ru counterparts. A variety of fused indoline compounds are synthesized using this method, including densely functionalized ring systems that are feasible due to base-free conditions. Experimental insights corroborate a cycloaddition initiated by nucleophilic attack at C3 of the indole radical cation by the vinyldiazo species.
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