Desilylative or Decarboxylative Photoadditions with Graphitic Carbon Nitride
Heterogeneous Visible-Light Photoredox Catalysis with Graphitic Carbon Nitride for α-Aminoalkyl Radical Additions, Allylations, and Heteroarylations.
ACS Catal. 2018;
14 December 2018 (online)
A graphitic carbon nitride (g-C3N4) catalyzed the desilylative addition of α-silylamines to alkenes or heteroaryl chlorides under visible-light irradiation to give the corresponding adducts in up to 96% yield (eq. 1). g-C3N4 also promoted the decarboxylative additions of α-amino acids to alkenes under similar conditions to afford the corresponding products in up to 79% yield (eq. 2).
In the desilylative addition of N-methyl-N-[(trimethylsilyl)methyl]aniline to 4-(2,2-dicyanoethenyl)toluene, g-C3N4 was reused eight times without significant loss of its catalytic activity. g-C3N4 was applied for the continuous-flow reaction of N-methyl-N-[(trimethylsilyl)methyl]aniline with cyclohexanone to afford the desired amine in 85% yield.