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Continuous-Flow Synthesis of Monoarylated Acetaldehydes Using Aryldiazonium Salts

Natalia Chernyak and Stephen L. Buchwald*

*Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, United States, Email:

N. Chernyak, S. L. Buchwald, J. Am. Chem. Soc., 2012, 134, 12466-12469.

DOI: 10.1021/ja305660a (free Supporting Information)


Anilines and ethyl vinyl ether can be combined in a safe continuous-flow process to achieve efficient and mono-selective formal α-arylation of acetaldehyde. The mild non-basic reaction conditions of this method allow for high functional group tolerance. This process also provides means for a safe and scalable generation of aryldiazonium salts and enables preparation of an array of synthetically valuable monoarylated acetaldehydes.

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Key Words

α-arylation, flow chemistry

ID: J48-Y2012-2480