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Using Anilines as Masked Cross‐Coupling Partners: Design of a Telescoped Three‐Step Flow Diazotization, Iododediazotization, Cross‐Coupling Process
Author(s) -
Teci Matthieu,
Tilley Michael,
McGuire Michael A.,
Organ Michael G.
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603626
Subject(s) - sonogashira coupling , aryl , coupling (piping) , substrate (aquarium) , process (computing) , flow (mathematics) , chemistry , continuous flow , solubility , sequence (biology) , iodide , combinatorial chemistry , materials science , process engineering , computer science , palladium , organic chemistry , catalysis , engineering , physics , mechanics , composite material , alkyl , oceanography , operating system , geology , biochemistry
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.