Synthesis of Sterically Hindered Primary Amines by Concurrent Tandem Photoredox CatalysisClick to copy article linkArticle link copied!
- Michael C. NicastriMichael C. NicastriDepartment of Chemistry, Columbia University, New York, New York 10027, United StatesMore by Michael C. Nicastri
- Dan Lehnherr*Dan Lehnherr*[email protected]Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United StatesMore by Dan Lehnherr
- Yu-hong LamYu-hong LamComputational and Structural Chemistry, Merck & Co., Inc., Rahway, New Jersey 07065, United StatesMore by Yu-hong Lam
- Daniel A. DiRoccoDaniel A. DiRoccoProcess Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United StatesMore by Daniel A. DiRocco
- Tomislav Rovis*Tomislav Rovis*[email protected]Department of Chemistry, Columbia University, New York, New York 10027, United StatesMore by Tomislav Rovis
Abstract

Primary amines are an important structural motif in active pharmaceutical ingredients (APIs) and intermediates thereof, as well as members of ligand libraries for either biological or catalytic applications. Many chemical methodologies exist for amine synthesis, but the direct synthesis of primary amines with a fully substituted α carbon center is an underdeveloped area. We report a method which utilizes photoredox catalysis to couple readily available O-benzoyl oximes with cyanoarenes to synthesize primary amines with fully substituted α-carbons. We also demonstrate that this method enables the synthesis of amines with α-trifluoromethyl functionality. Based on experimental and computational results, we propose a mechanism where the photocatalyst engages in concurrent tandem catalysis by reacting with the oxime as a triplet sensitizer in the first catalytic cycle and a reductant toward the cyanoarene in the second catalytic cycle to achieve the synthesis of hindered primary amines via heterocoupling of radicals from readily available oximes.
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