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Nickel-Catalyzed Annulation of Aliphatic Amides with Alkynyl­silanes: An Expeditious Approach to Five-Membered Lactams

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An expeditious approach for the synthesis of diverse five-membered lactams through nickel-catalyzed annulation of the C(sp3)–H bonds of aliphatic amides with alkynylsilanes assisted by an 8-aminoquinolinyl directing group is reported,… Click to show full abstract

An expeditious approach for the synthesis of diverse five-membered lactams through nickel-catalyzed annulation of the C(sp3)–H bonds of aliphatic amides with alkynylsilanes assisted by an 8-aminoquinolinyl directing group is reported, delivering the corresponding lactam derivatives in moderate to high yields. It is worth noting that alkynylsilanes are employed for the first time as coupling partners in the transition-metal-catalyzed functionalization of C(sp3)–H bonds of aliphatic amides. Equimolar amounts of alkynylsilanes and aliphatic amides are utilized, which greatly increases the efficiency of this protocol.

Keywords: five membered; expeditious approach; aliphatic amides; membered lactams; nickel catalyzed; catalyzed annulation

Journal Title: Synlett
Year Published: 2020

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