Abstract
The phenolate anion was developed as a new photocatalyst with strong reduction potentials (−3.16 V vs. SCE) to reduction of aryl halides to aryl radicals through single electron transfer.
Highlights
Since the chemical reactivity of electronically excited molecules differs fundamentally from that of those in the ground state, the photochemistry induced by visible light provides fresh opportunities to expand the potential of organic chemistry
We discovered that the visible light-excited vinylphenolate anions enabled the direct reduction of aryl halides to aryl radicals.[4]
On the basis of our previous work,[4] we proposed that a single electron transfer (SET) process between the excited phenolate anion B* and aryl halide D could occur to produce a phenoxyl radical C and an aryl radical E
Summary
Since the chemical reactivity of electronically excited molecules differs fundamentally from that of those in the ground state, the photochemistry induced by visible light provides fresh opportunities to expand the potential of organic chemistry. Aryl chlorides without electron withdrawing substituents are still a poorly accessible substrate for currently known visible light photocatalysts due to their large negative reduction potentials.[12] Here, we demonstrated the application of the colored phenolate anion as a new visible light photocatalyst for the catalytic generation of (hetero)aryl radicals from non-activated (hetero)aryl halides and the successful development of an operationally simple and redox-neutral protocol for the intermolecular oxyarylation of a wide range of ole ns (Scheme 1c).
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