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Synfacts 2019; 15(01): 0071
DOI: 10.1055/s-0037-1611166
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart · New York

Desilylative or Decarboxylative Photoadditions with Graphitic Carbon Nitride

Contributor(s):
Yasuhiro Uozumi
,
Ryoko Niimi
Cai Y, Tang Y, Fan L, Lefebvre Q, Hou H, Rueping M. * RWTH Aachen University, Germany; King Abdullah University of Science and Technology, Thuwal, Saudi Arabia; Chongqing University, P. R. of China
Heterogeneous Visible-Light Photoredox Catalysis with Graphitic Carbon Nitride for α-Aminoalkyl Radical Additions, Allylations, and Heteroarylations.

ACS Catal. 2018;
8: 9471-9476
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Publication History

Publication Date:
14 December 2018 (online)

 
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Key words

photocatalysis - aminoalkyl radical addition - carbon nitride

Significance

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).


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Comment

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.


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