Alpha-arylation of 3-benzazepin-2-ones with microwave heating

Totally Microwave

I came across an interesting article on alpha arylation of a 3-benzazepin-2-one, which is a particularly sluggish reaction (TL 2013). First thing is first, the formation of a traditional amide enolate with n-BuLi doesn’t effectively alkylate with simple substrates and the use of NaH was needed as the base to obtain the desired reaction (this was back in 1979), which was not going to be a good starting point for arylation. Unfortunately, the addition of Pd into the cycle did not produce any of the desired product so the base strength was a consideration as an issue. The addition of Cu2I2 from Li and Na amide enolates provided the first successful formation of the desired material with heat helping the reaction along (and effectively forming a Cu-amide enolate that can transmetallate). A switch from Li to Na improved the process, but examining solvent and the best Pd source…

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