Abstract
An acyl radical generation and functionalization strategy through direct photoexcitation of benzothiazolines has been developed. The formed acyl radical species can either be trapped by quinoxalin-2-ones to realize their C(3)-H functionalization or trigger a cascade radical cyclization with isonitriles to synthesise biologically important phenanthridines. The synthetic value of this protocol can be further illustrated by the modification of quinoxalin-2-ones, containing important natural products and drug-based complex molecules.
Highlights
Radical generation involving the utilization of visible light as a green and sustainable energy source has been developed remarkably in the past several years [1,2,3,4,5,6,7,8]
Among the above-mentioned strategies, direct photoexcitation of reaction substrates is the most straightforward manner to generate radicals, in which the radical precursor itself can absorb visible light and the acquired energy is involved in bond cleavage for radical generation (Scheme 1a)
During our investigation on the photochemical mation of C(2)-substituted benzothiazolines, we found have thehave ability transformation of C(2)-substituted benzothiazolines, wethose foundsubstrates those substrates the to absorb visible light, which led us to explore the potential reactivity of
Summary
Radical generation involving the utilization of visible light as a green and sustainable energy source has been developed remarkably in the past several years [1,2,3,4,5,6,7,8]. Melchiorre group found that direct photoexcitation of 4-R-1,4-dihydropyridines (R-DHPs) resulted in the formation of an R radical, which was further utilized in cross-coupling reactions using Nickle complex as an electron mediator [33,34,35,36]. Despite those elegant contributions, continuous exploration of novel and accessible photo-sensitive molecules such as radical precursors and further expansion of the reaction types of photo-generated radical species into the synthesis of biologically important heterocyclic compounds, is still highly desirable and appealing
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