Brønsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C-C Bond Formation via Amidyl Radicals

Jiaqi Jia; Yee Ann Ho; Raoul F Bülow; Magnus Rueping

doi:10.1002/chem.201802907

Brønsted Base Assisted Photoredox Catalysis: Proton Coupled Electron Transfer for Remote C-C Bond Formation via Amidyl Radicals

Chemistry. 2018 Sep 20;24(53):14054-14058. doi: 10.1002/chem.201802907. Epub 2018 Aug 27.

Authors

Jiaqi Jia¹, Yee Ann Ho¹, Raoul F Bülow¹, Magnus Rueping^{1

2}

Affiliations

¹ Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52074, Aachen, Germany.
² King Abdullah University of Science and Technology (KAUST), KAUST Catalysis Center (KCC), Thuwal, 23955-6900, Saudi Arabia.

PMID: 29939456
DOI: 10.1002/chem.201802907

Abstract

The synthesis of alkyne- and alkene-decorated lactams has been achieved through a photoredox-initiated radical cascade reaction. The developed Brønsted base assisted, photoredox-catalyzed, intramolecular 5-exo-trig cyclization/intermolecular radical addition/elimination reaction provides facile access to functionalized γ-lactams, with good functional group tolerance and high yields.

Keywords: Brønsted base; lactam derivatives; photoredox catalysis; proton-coupled electron transfer (PCET); radical reactions; sulfonyl radical.