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Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles

, : Light-Induced Direct Arylation in the Solid Crystalline State as a Strategy Towards π-Expanded Imidazoles. Chemistry, An Asian Journal 11(18): 2513-2517

π-Expanded imidazoles bearing the 2-iodophenyl substituent at position 2 undergo direct photoinduced intramolecular arylation in the solid, crystalline state leading to large non-planar heterocycles. An analogous reaction employing 2-bromophenyl and 2-chlorophenyl substituents is considerably slower. Such processes have never before been demonstrated to occur in crystals and have allowed the efficient synthesizes of structurally unique compounds containing either the phenanthro[9',10':4,5]imidazo[1,2-f]phenanthridine moiety or structurally related skeletons. The reaction occurs in the thin crystalline layers irradiated with UV photons in an almost quantitative manner over 48-72 h. Several previously unknown architectures have been prepared using this methodology. Furthermore, the optical properties of these π-expanded imidazoles can be altered with the addition of heteroatoms and/or electron-donating groups.


PMID: 27452918

DOI: 10.1002/asia.201600752

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