Directed Zincation with TMPZnCl·LiCl and Further Functionalization of the Tropolone Scaffold.
Diana HaasDaniela Sustac-RomanSophia SchwarzPaul KnochelPublished in: Organic letters (2016)
The directed zincation of tropolone derivatives was achieved using TMPZnCl·LiCl. Various functionalizations of the zincated intermediates by halogenation, acylation, allylation, and Negishi cross-coupling were successfully performed. Additionally, 1,8-conjugate addition-elimination reactions with a variety of arylmagnesium and secondary alkylzinc reagents were carried out to further elaborate the tropolone core.