Although the use of Grignard reagents is successfully
obviated, the main downside of this stepwise procedure
is that the hydrogenation step might be incompatible with
various functional groups on the indole core such as nitro and
bromine, groups that could allow for further functionalization.
Both Pei’s and Hossain’s strategy are similar in that they both
generate a benzylic alkoxide that undergoes [1,2]-arylmigration
via displacement of a suitable leaving group at the R-position.
On the other hand, the two strategies differ with regard to the
nucleophile used, and while one occurs in a basicmedia, the other
one is acid catalyzed. Here, we report a simple and straightforward
addition of ethyl diazoacetate to readily available