26902-03-4Relevant academic research and scientific papers
Effective Utilization of NIR Wavelengths for Photo-Controlled Polymerization: Penetration Through Thick Barriers and Parallel Solar Syntheses
Wu, Zilong,Jung, Kenward,Boyer, Cyrille
, p. 2013 - 2017 (2020)
This contribution details an efficient and controlled photopolymerization regulated by far-red (λ=680 nm) and NIR (λ=780 and 850 nm) light in the presence of aluminium phthalocyanine and aluminium naphthalocyanine. Initiating radicals are generated by photosensitization of peroxides affording an effective strategy that provides controlled polymerization of a variety of monomers with excellent living characteristics. Critically, long wavelength irradiation provides penetration through thick barriers, affording unprecedented rates of controlled polymerization that can open new and exciting applications. Furthermore, a more optimized approach to performing solar syntheses is presented. By combining the narrow Q-bands of these photocatalysts with others possessing complementary absorptions, layered, independent polymerizations and organic transformations may be performed in parallel under a single broadband emission source, such as sunlight.
Radical functionalization of thioglycosides in aqueous medium
Kaur, Sarbjeet,Luciano, Dominic P.,Fan, Xinhao,Zhao, Gaoyuan,Messier, Sheridan,Walker, Madison M.,Zhang, Qiang,Wang, Ting
, (2021/11/08)
A visible-light-mediated thiol-ene reaction is successfully operated in aqueous medium. An organic photoredox catalyst (9-mesityl-10-methylacridinum tetrafluoroborate) is used to initiate the radical process to generate thiyl radicals upon light irradiation. Two reaction pathways were discovered in different aqueous buffer systems. A thiol-ene adduct is preferred in acidic reaction medium; while disulfide formation is found to be favored in basic reaction medium. The photocatalytic method is demonstrated to be applicable on unprotected peptides.
Metal-free photocatalytic thiol-ene/thiol-yne reactions
Kaur, Sarbjeet,Zhao, Gaoyuan,Busch, Evan,Wang, Ting
supporting information, p. 1955 - 1961 (2019/02/20)
The organic photocatalyst (9-mesityl-10-methylacridinum tetrafluoroborate) in the presence of visible light is used to initiate thiol-ene and thiol-yne reactions. Thiyl radicals are generated upon quenching the photoexcited catalyst with a range of thiols
Visible-Light-Mediated Organocatalyzed Thiol-Ene Reaction Initiated by a Proton-Coupled Electron Transfer
Levin, Vitalij V.,Dilman, Alexander D.
, p. 8337 - 8343 (2019/06/27)
A convenient method for performing a thiol-ene reaction is described. The reaction is performed under blue-light irradiation and catalyzed by photoactive Lewis basic molecules such as acridine orange or naphthalene-fused N-acylbenzimidazole. It is believed that the process is initiated by a proton-coupled electron transfer process within the complex between the thiol and the Lewis basic catalyst.
Photoinitiated Thiol-Ene “Click” Reaction: An Organocatalytic Alternative
Limnios, Dimitris,Kokotos, Christoforos G.
supporting information, p. 323 - 328 (2017/02/05)
The thiol-ene coupling (TEC) reaction has attracted a lot of scientific attention during the last years, particularly in the fields of polymers, materials and more recently in drug design. The combination of organocatalysis and photocatalysis has enabled the development of an efficient synergistic protocol for the addition of various thiols to a plethora of olefins. Utilizing phenylglyoxylic acid as the catalyst-initiator and common household bulbs as the light source, we report an organocatalytic photoinitiated TEC reaction showing exceptional tolerance in the presence of various functionalities, untangling previously unsolved problems. (Figure presented.).
Visible-Light-Mediated Thiol-Ene Reactions through Organic Photoredox Catalysis
Zhao, Gaoyuan,Kaur, Sarbjeet,Wang, Ting
supporting information, p. 3291 - 3294 (2017/06/23)
Synthetically useful radical thiol-ene reactions can be initiated by visible-light irradiation in the presence of an organic photocatalyst, 9-mesityl-10-methylacridinum tetrafluoroborate. The key thiyl radical intermediates are generated upon quenching of
Transition metal photoredox catalysis of radical thiol-ene reactions
Tyson, Elizabeth L.,Ament, Michael S.,Yoon, Tehshik P.
, p. 2046 - 2050 (2013/03/29)
We describe the anti-Markovnikov hydrothiolation of olefins using visible-light-absorbing transition metal photocatalysts. The key thiyl radical intermediates are generated upon quenching of photoexcited Ru*(bpz) 32 with a variety of thiols. The adducts of a wide variety of olefins and thiols are formed in excellent yield (73-99%).
