Homogeneous and Gas–Liquid Catellani‐Type Reaction Enabled by Continuous‐Flow Chemistry. Issue 53 (28th August 2018)

• Record Type: Journal Article
• Authors: Casnati, Alessandra; Gemoets, Hannes P. L.; Motti, Elena; Della Ca', Nicola; Noël, Timothy
• Is Part Of: Chemistry. Volume 24:Issue 53(2018)
• Page Start: 14079
• Page End: 14083
• Publication Date: 2018-08-28
• Subjects: C−H functionalization -- Catellani reaction -- flow chemistry -- gas–liquid -- homogeneous; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.201803909
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: A practical homogeneous and gas‐liquid palladium‐catalyzed Catellani‐type reaction using a continuous‐flow platform is described. The implementation of continuous‐flow technology allowed the acceleration of the transformation and, for the first time, expansion of the chemical space to gaseous olefins (i.e., ethylene, propylene and 3, 3, 3‐trifluoropropene), thus providing a safe and practical approach to sterically hindered ortho ‐disubstituted styrenes and vinyl arenes. The complete control over the stoichiometry of gaseous reagents through flow technology proved essential for directing the selectivity of the Catellani reaction to the desired products. Abstract : Hit the gas : A practical continuous‐flow platform enabling both homogeneous and gas–liquid Catellani‐type reactions is described. The implementation of continuous‐flow technology allowed to accelerate the transformation and to expand the chemical space to gaseous olefins. The complete control over the stoichiometry of gaseous reagents was deemed essential to direct selectivity, thus providing a practical approach to sterically hindered ortho ‐disubstituted styrenes and vinyl arenes.