5 years ago

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

Synthesis of Heterocycle-Containing 9,9-Diarylfluorenes Using Superelectrophiles
Tomohiko Ohwada, Akinari Sumita, Douglas A Klumpp, Makafui Gasonoo, Kristen Giuffre, Kenneth N. Boblak
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.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b00311

DOI: 10.1021/acs.joc.7b00311

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