Synthesis of Heterocycle-Containing 9,9-Diarylfluorenes Using Superelectrophiles.


A superacid-promoted method for the synthesis of 9,9-diarylfluorenes is described. The chemistry involves cyclizations and arylations with biphenyl-substituted heterocyclic ketones and a mechanism is proposed involving superelectrophilic intermediates. The key reactive intermediates-dicationic and trication fluorenyl cations have been observed by low-temperature NMR and the mechanism has been further studied using DFT calculations.

DOI: 10.1021/acs.joc.7b00311

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@article{Gasonoo2017SynthesisOH, title={Synthesis of Heterocycle-Containing 9,9-Diarylfluorenes Using Superelectrophiles.}, author={Makafui Gasonoo and Akinari Sumita and Kenneth N Boblak and Kristen Giuffre and Tomohiko Ohwada and Douglas A Klumpp}, journal={The Journal of organic chemistry}, year={2017}, volume={82 12}, pages={6044-6053} }