Iridium‐Catalyzed Formyl‐Selective Deuteration of Aldehydes. Issue 27 (7th June 2017)

• Record Type: Journal Article
• Authors: Kerr, William J.; Reid, Marc; Tuttle, Tell
• Is Part Of: Angewandte Chemie international edition. Volume 56:Issue 27(2017)
• Page Start: 7808
• Page End: 7812
• Publication Date: 2017-06-07
• Subjects: aldehydes -- C−H activation -- deuteration -- DFT -- iridium; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201702997
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: We report the first direct catalytic method for formyl‐selective deuterium labeling of aromatic aldehydes under mild conditions, using an iridium‐based catalyst designed to favor formyl over aromatic C−H activation. A good range of aromatic aldehydes is selectively labeled, and a one‐pot labeling/olefination method is also described. Computational studies support kinetic product control over competing aromatic labeling and decarbonylation pathways. Abstract : Al(D)hydes : An iridium catalyst system was designed to effect formyl over aryl C−H activation of aromatic aldehydes. Computational studies support kinetic product control over competing aromatic labeling and decarbonylation pathways.