US EPA

7469013 

Journal Article 

Photoredox-Catalyzed Ketyl-Olefin Coupling for the Synthesis of Substituted Chromanols 

Fava, E; Nakajima, M; Nguyen, ALP; Rueping, M 

2016 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

American Chemical Society 

81 

16 

6959-6964 

English 

10.1021/acs.joc.6b01006 

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. 

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