NDLI: A synergistic LUMO lowering strategy using Lewis acid catalysis in water to enable photoredox catalytic, functionalizing C–C cross-coupling of styrenes† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc02106f

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A synergistic LUMO lowering strategy using Lewis acid catalysis in water to enable photoredox catalytic, functionalizing C–C cross-coupling of styrenes† †Electronic supplementary information (ESI) available. See DOI: 10.1039/c8sc02106f

Content Provider	Semantic Scholar
Author	Speckmeier, Elisabeth Fuchs, Patrick J. W. Zeitler, Kirsten
Copyright Year	2018
Abstract	Easily available α-carbonyl acetates serve as convenient alkyl radical source for an efficient, photocatalytic cross-coupling with a great variety of styrenes. Activation of electronically different α-acetylated acetophenone derivatives could be effected via LUMO lowering catalysis using a superior, synergistic combination of water and (water-compatible) Lewis acids. Deliberate application of fac-Ir(ppy)3 as photocatalyst to enforce an oxidative quenching cycle is crucial to the success of this (umpolung type) transformation. Mechanistic particulars of this dual catalytic coupling reaction have been studied in detail using both Stern-Volmer and cyclic voltammetry experiments. As demonstrated in more than 30 examples, our water-assisted LA/photoredox catalytic activation strategy allows for excess-free, equimolar radical cross-coupling and subsequent formal Markovnikov hydroxylation to versatile 1,4-difunctionalized products in good to excellent yields.
Starting Page	7096
Ending Page	7103
Page Count	8
File Format	PDF HTM / HTML
DOI	10.1039/c8sc02106f
PubMed reference number	30310630
Journal	Medline
Volume Number	9
Alternate Webpage(s)	https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/8c/77/SC-009-C8SC02106F.PMC6137453.pdf
Alternate Webpage(s)	https://pubs.rsc.org/en/content/articlepdf/2018/sc/c8sc02106f
Alternate Webpage(s)	http://www.rsc.org/suppdata/c8/sc/c8sc02106f/c8sc02106f1.pdf
Journal	Chemical science
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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