title: Discovery of an α-amino C-H arylation reaction using the strategy of accelerated serendipity.
abstract: Serendipity has long been a welcome yet elusive phenomenon in the advancement of chemistry. We sought to exploit serendipity as a means of rapidly identifying unanticipated chemical transformations. By using a high-throughput, automated workflow and evaluating a large number of random reactions, we have discovered a photoredox-catalyzed C-H arylation reaction for the construction of benzylic amines, an important structural motif within pharmaceutical compounds that is not readily accessed via simple substrates. The mechanism directly couples tertiary amines with cyanoaromatics by using mild and operationally trivial conditions.
authors: Merck Center for Catalysis, Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.
authors: Andrew
authors: A
authors: McNally
authors: Christopher K
authors: CK
authors: Prier
authors: David W C
authors: DW
authors: MacMillan
mesh_terms: D000586:Amination; D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry*; D001555:Benzene Derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D002244:Carbon / Q000737:chemistry; D002384:Catalysis; D008401:Gas Chromatography-Mass Spectrometry; D006571:Heterocyclic Compounds / Q000737:chemistry; D057166:High-Throughput Screening Assays; D006859:Hydrogen / Q000737:chemistry; D055601:Organic Chemistry Phenomena; D010084:Oxidation-Reduction; D055668:Photochemical Processes
chemical_list: D000588:Amines; D001555:Benzene Derivatives; D006571:Heterocyclic Compounds; D002244:Carbon; D006859:Hydrogen