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

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 t...

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Veröffentlicht in:Journal of organic chemistry 2017-06, Vol.82 (12), p.6044-6053
Hauptverfasser: Gasonoo, Makafui, Sumita, Akinari, Boblak, Kenneth N, Giuffre, Kristen, Ohwada, Tomohiko, Klumpp, Douglas A
Format: Artikel
Sprache:eng
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Zusammenfassung: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b00311