Isoindoles are naturally occurring heterocyclic compounds that have can function as pharmaceutical agents and as organic light emitting devices (OLEDs). There are currently various methods of producing these compounds through organometallic catalysis which utilize Lewis acids to form ring structures from benzonitriles and amines. However, most methods have several steps that require isolation of intermediates and significant amounts of metal catalysts. Utilizing Pd(OAc)2 at a 0.5 mole percent scale and Ga(OTf)3 as a Lewis acid, our goal was to utilize relay catalysis to synthesize 3-ethoxyisoindoles from 2-iodobenzonitrile and various alkynes in ethanol in a more green and time-efficient manner. Running one-pot reactions for 24 h, we found that the cross-coupling step was complete after 1 h for all alkynes used. Cyclization forming was complete within 24 h for phenylacetylenes with electron withdrawing groups or weakly electron donating groups. These results show that we have developed a simple cleaner method for producing 3-ethoxyisoindoles that may be implemented to further study their applications.

Relay catalysis approach for the synthesis of 3-ethoxy-1-H-isoindoles

254th National Meeting (2017)

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