title: Using Anilines as Masked Cross-Coupling Partners: Design of a Telescoped Three-Step Flow Diazotization, Iododediazotization, Cross-Coupling Process.
abstract: 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.
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J 1P3, Canada.
authors.forename: Matthieu
authors.initials: M
authors.lastname: Teci
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J 1P3, Canada.
authors.forename: Michael
authors.initials: M
authors.lastname: Tilley
authors.affiliation: GlaxoSmithKline Pharmaceuticals Inc., 709 Swedeland Rd. PO Box 1539, UMW 2810, King of Prussia, PA, 19406, USA.
authors.forename: Michael A
authors.initials: MA
authors.lastname: McGuire
authors.affiliation: Department of Chemistry, York University, 4700 Keele Street, Toronto, Ontario, M3J 1P3, Canada.|Centre for Catalysis Research and Innovation and Department of Chemistry, University of Ottawa, Ottawa, Ontario, K1N 6N5, Canada.
authors.forename: Michael G
authors.initials: MG
authors.lastname: Organ
keywords: anilines; cross-coupling; diazotization; flow conditions; sustainable chemistry