Regioselective Synthesis of Unsymmetric Tetra- and Pentasubstituted Pyrenes with a Strategy for Primary C-Alkylation at the 2-Position.
Ana M DmytrejchukSydney N JacksonRolande MeudomJohn D GordenBradley L MernerPublished in: The Journal of organic chemistry (2018)
The synthesis of 1,2,4,5- and 1,2,9,10-tetrasubstituted and 1,2,4,5,8-pentasubsutituted pyrenes has been achieved by initially functionalizing the K-region of pyrene. Bromination, acylation, and formylation reactions afford high to moderate levels of regioselectivity, which facilitate the controlled introduction of other functional groups about 4,5-dimethoxypyrene. Access to 4,5-dimethoxypyren-1-ol and 9,10-dimethoxypyren-1-ol enabled a rare, C-2 primary alkyl substitution of pyrene.
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