Direct Regioselective Oxidative Cross-Coupling of Indoles with Methyl Ketones: A Novel Route to C3-Dicarbonylation of Indoles

The first C3-dicarbonylation of indoles
was realized through direct
oxidative cross-coupling of indoles with methyl ketones in the presence
of molecular iodine and pyrrolidine. This reaction constructed a highly
efficient indolyl diketones scaffold, which might be regarded as a
useful biological and pharmacological tool in the exploration of therapeutic
A2BAR modulators. The use of inexpensive molecular iodine
and pyrrolidine and a broad substrate scope make this protocol very
practical. Preliminary mechanistic studies indicate that two paths
are involved in this process.