Indole Synthesis through Sequential Electrophilic N-H and C-H Bond Activation Using Iodine(III) Reactivity.

Published in: Chemistry (Weinheim an der Bergstrasse, Germany) (2016)

An intramolecular approach towards the regioselective construction of 2,3-diarylated indoles is reported. The reaction follows an intramolecular electrophilic N-H and C-H bond functionalization between the aniline and acetylene. This methodology employs the concept of a traceless tether to provide access to the free 2,3-diarylated indole products comprising a total of 18 examples. Hypervalent iodine reagents were identified as suitable promoters and four different protocols are provided, including stoichiometric and catalytic transformations.

Keyphrases

dual energy
energy transfer
electron transfer
transition metal
computed tomography
contrast enhanced