Using Anilines as Masked Cross‐Coupling Partners: Design of a Telescoped Three‐Step Flow Diazotization, Iododediazotization, Cross‐Coupling Process

The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three‐reactor flow diazotization/iododediazotization/cross‐coupling process. The segmented flow stream created by off‐gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous‐flow unit controlled by custom software created in‐house. The resultant aryl iodide was then combined with a stream of cross‐coupling solution that fed into the final reactor. The system proved versatile as modifications to the diazotization/iododediazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki–Miyaura and Sonogashira cross‐coupled products.