Chiral N, N Ligands Enabling Palladium‐Catalyzed Enantioselective Intramolecular Heck–Matsuda Carbonylation Reactions by Sequential Migratory and CO Insertions. Issue 37 (17th August 2018)

• Record Type: Journal Article
• Authors: Carmona, Rafaela C.; Köster, Otto D.; Correia, Carlos Roque Duarte
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 37(2018)
• Page Start: 12067
• Page End: 12070
• Publication Date: 2018-08-17
• Subjects: asymmetric catalysis -- cascade reactions -- Heck reaction -- N, N ligands -- palladium catalysis; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201805831
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Unprecedented enantioselective intramolecular Heck carbonylation reactions of arenediazonium salts were enabled by a chiral N, N ligand. This reaction constitutes the first enantioselective Heck carbonylation that proceeds through migratory insertion followed by CO insertion. The enantioenriched functionalized dihydrobenzofurans were obtained in good to high yields and enantiomeric ratios of up to 98:2 under mild and operationally simple reaction conditions. Abstract : Enantioselective intramolecular Heck carbonylations of arenediazonium salts are enabled by a palladium catalyst in combination with a chiral N, N ligand. Enantioenriched dihydrobenzofurans were obtained through an unprecedented sequence of migratory insertion followed by CO insertion.