Silver-Catalyzed, N-Formylation of Amines Using Glycol Ethers
Bradley H King1, Michelle L Wang1, Kate A Jesse1
1Keck Science Department, Scripps, Claremont McKenna and Pitzer Colleges, Claremont, California 91711, United States.
Abstract:
A silver-catalyzed protocol was found to afford the N-formylation of amines in moderate-to-good yields. Ethylene glycol-derived, oligomeric ethers were found to function as the formylating agent, with 1,4-dioxane affording the best results. This reaction does not require the use of stoichiometric activating reagents, and avoids the use of explosive reagents or toxic gases, such as CO, as the C1 synthon. Mechanistic studies indicate a single-electron transfer-based pathway. This work highlights the ability of silver to participate in unexpected reaction pathways.
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