Synergistic Brønsted/Lewis Acid Catalyzed Aromatic Alkylation with Unactivated Tertiary Alcohols or Di-tert-Butylperoxide to Synthesize Quaternary Carbon Centers
Keyword(s):
Dual Brønsted/Lewis acid catalysis involving environmentally benign, readily accessible protic acid and iron promotes site-selective tert-butylation of electron-rich arenes using di-tert-butylperoxide. This transformation inspired the development of a synergistic Brønsted/Lewis acid catalyzed aromatic alkylation that fills a gap in the Friedel–Crafts reaction literature by employing unactivated tertiary alcohols as alkylating agents, leading to new quaternary carbon centers. Corroborated by DFT calculations, the Lewis acid serves a role in enhancing the acidity of the Brønsted acid. The use of non-allylic, non-benzylic, and non-propargylic tertiary alcohols represents an underexplored area in Friedel–Crafts reactivity.
2019 ◽
Vol 58
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pp. 15386-15389
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2004 ◽
Vol 69
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pp. 4412-4428
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2011 ◽
Vol 353
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pp. 563-568
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2013 ◽
Vol 52
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pp. 3485-3489
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2015 ◽
Vol 21
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pp. 17565-17569
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