Photoredox-Catalyzed Ketyl-Olefin Coupling for the Synthesis of Substituted Chromanols
Fava, E; Nakajima, M; Nguyen, ALP; Rueping, M
| HERO ID | 7469013 |
|---|---|
| In Press | No |
| Year | 2016 |
| Title | Photoredox-Catalyzed Ketyl-Olefin Coupling for the Synthesis of Substituted Chromanols |
| Authors | Fava, E; Nakajima, M; Nguyen, ALP; Rueping, M |
| Journal | Journal of Organic Chemistry |
| Volume | 81 |
| Issue | 16 |
| Page Numbers | 6959-6964 |
| Abstract | A visible light photoredox-catalyzed aldehyde olefin cyclization is reported. The method represents a formal hydroacylation of alkenes and alkynes and provides chromanol derivatives in good yields. The protocol takes advantage of the double role played by trialkylamines (NR3) which act as (i) electron donors for reducing the catalyst and (ii) proton donors to activate the substrate via a proton-coupled electron transfer. © 2016 American Chemical Society. |
| Doi | 10.1021/acs.joc.6b01006 |
| Is Certified Translation | No |
| Dupe Override | No |
| Comments | Scopus URL: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84983319691&doi=10.1021%2facs.joc.6b01006&partnerID=40&md5=0c58bc5fb5bd74e2a1751eb4c5d583e9 |
| Is Public | Yes |
| Language Text | English |
| Keyword | Catalysis; Hydrocarbons; Olefins; Chromanol; Electron donors; Hydroacylation; Proton coupled electron transfers; Proton donors; Visible light; Cyclization; 2 benzyl 2,3 dihydro 1h inden 1 ol; 3 (3 methylbenzylidene)chroman 4 ol; 3 (4 methoxybenzyl)chroman 4 ol; 3 (4 methoxybenzylidene)chroman 4 ol; 3 benzhydrylchroman 4 ol; 3 benzyl 6 bromochroman 4 ol; 3 benzyl 6 fluorochroman 4 ol; 3 benzyl 6 methoxychroman 4 ol; 3 benzyl 6,8 di tert butylchroman 4 ol; 3 benzyl 7 methoxychroman 4 ol; 3 benzyl 8 ethoxychroman 4 ol; 3 benzyl 8 methylchroman 4 ol; 3 benzyl 8 phenylchroman 4 ol; 3 benzylchroman 4 ol; aldehyde; alkene derivative; alkyne derivative; antivirus agent; chroman derivative; chromanol derivative; ketyl; methyl 3 benzyl 4 hydroxychroman 6 carboxylate; tert butyl(3 benzyl 4 hydroxychroman 6 yl)carbamate; unclassified drug; acylation; antiviral activity; Article; chemical analysis; chemical reaction; cross coupling reaction; cyclization; drug synthesis; electron transport; human; oxidation reduction potential; photocatalysis; reaction analysis |