The Dark Side of Isocyanides: Visible-Light Photocatalytic Activity in the Oxidative Functionalization of C(sp3)-H Bonds

The possibility to harness aromatic isocyanides as visible-light photocatalysts in the a-amino C(sp(3))-H functionalization is herein presented. Actually, the three-component crossdehydrogenative coupling of aromatic tertiary amines with isocyanides and water leads to amide products under very mild conditions in high yields and with a good substrate scope. While the reaction with aromatic isocyanides proceeds upon direct photoexcitation, aliphatic isocyanides are able to form a photoactive electron-donor-acceptor complex with aromatic amines. Moreover, the use of a catalytic loading of an aromatic isocyanide promotes the oxidative coupling of N-phenyl-1,2,3,4-tetrahydroisoquinoline with an array of different (pro)nucleophiles in good to excellent yields, thus providing the proof-of-concept for the development of a new highly tunable class of organic visible-light photocatalysts.

Automated summary

This study demonstrates the potential of using aromatic isocyanides as visible-light photocatalysts for a-amino C(sp(3))-H functionalization, successfully achieving a three-component crossdehydrogenative coupling reaction with high yields and a good substrate scope. The use of a catalytic loading of aromatic isocyanide also promotes the oxidative coupling of N-phenyl-1,2,3,4-tetrahydroisoquinoline with various different (pro)nucleophiles, showing promise in developing a new class of highly tunable organic visible-light photocatalysts.