3279-79-6Relevant academic research and scientific papers
Lewis Basic Salt-Promoted Organosilane Coupling Reactions with Aromatic Electrophiles
Reidl, Tyler W.,Bandar, Jeffrey S.
supporting information, p. 11939 - 11945 (2021/08/20)
Lewis basic salts promote benzyltrimethylsilane coupling with (hetero)aryl nitriles, sulfones, and chlorides as a new route to 1,1-diarylalkanes. This method combines the substrate modularity and selectivity characteristic of cross-coupling with the practicality of a base-promoted protocol. In addition, a Lewis base strategy enables a complementary scope to existing methods, employs stable and easily prepared organosilanes, and achieves selective arylation in the presence of acidic functional groups. The utility of this method is demonstrated by the synthesis of pharmaceutical analogues and its use in multicomponent reactions.
Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light
Liu, Peng,Liu, Wenbo,Li, Chao-Jun
supporting information, p. 14315 - 14321 (2017/10/17)
The Minisci alkylation is useful to functionalize aromatics via alkyl radical addition. Current approaches to prepare alkyl radicals follow either oxidative or reductive pathways from various functional groups. Developing new strategy beyond these traditional methods remains elusive yet highly significant. In this article, we present a redox-neutral and catalyst-free protocol to engender alkyl radicals in the context of trifluoromethylation and general alkylation of arenes. This protocol, via the Norrish type I concept to produce alkyl radicals, accommodates various functional groups and delivers the product in good yields. This method identified a series of compounds as the trifluoromethylation and alkylation reagents assisted by light. It is expected that these compounds can find potential applications in other radical-involved reactions.
Eosin Y (EY) Photoredox-Catalyzed Sulfonylation of Alkenes: Scope and Mechanism
Meyer, Andreas Uwe,Straková, Karolína,Slanina, Tomá?,K?nig, Burkhard
supporting information, p. 8694 - 8699 (2016/07/07)
Alkyl- and aryl vinyl sulfones were obtained by eosin Y (EY)-mediated visible-light photooxidation of sulfinate salts and the reaction of the resulting S-centered radicals with alkenes. Optimized reaction conditions, the sulfinate and alkene scope, and X-ray structural analyses of several reaction products are provided. A detailed spectroscopic study explains the reaction mechanism, which proceeds through the EY radical cation as key intermediate oxidizing the sulfinate salts.
Dioxygen-Mediated Decarbonylative C-H Alkylation of Heteroaromatic Bases with Aldehydes
Paul, Subhasis,Guin, Joyram
supporting information, p. 17618 - 17622 (2015/12/05)
An operationally simple and economical method for the direct alkylation of heteroaromatic bases employing readily available aldehydes as alkyl radical precursors and molecular oxygen as a reagent is presented. This simple transformation demonstrates a broad substrate scope with respect to aldehydes and nitrogen heterocycles, enabling the introduction of several medicinally important yet challenging alkyl moieties, such as ethyl, isopropyl, tert-butyl, and cyclohexyl to the different classes of heterocyclic bases in good to excellent yields. A simple method for the direct alkylation of heteroaromatic bases with aldehydes as inexpensive alkyl radical precursors and molecular oxygen as a reagent is presented. This transformation demonstrates a broad substrate scope with respect to aldehydes and nitrogen heterocycles, enabling the introduction of various alkyl moieties to heterocyclic bases (>40 examples) in good to excellent yields.
Practical and innate carbon-hydrogen functionalization of heterocycles
Fujiwara, Yuta,Dixon, Janice A.,O'Hara, Fionn,Funder, Erik Daa,Dixon, Darryl D.,Rodriguez, Rodrigo A.,Baxter, Ryan D.,Herle, Bart,Sach, Neal,Collins, Michael R.,Ishihara, Yoshihiro,Baran, Phil S.
, p. 95 - 99 (2013/02/23)
Nitrogen-rich heterocyclic compounds have had a profound effect on human health because these chemical motifs are found in a large number of drugs used to combat a broad range of diseases and pathophysiological conditions. Advances in transition-metal-med
Photochemical Reactions of Caffeine with Aliphatic Aldehydes
Erndt, Aleksander,Fiedorowicz, Maciej,Kostuch, Andrzej,Para, Andrzej
, p. 1043 - 1046 (2007/10/02)
Photochemical reactions of caffeine with several aliphatic aldehydes are performed.In the reactions with ethanal, propanal and butanal stable 8-acyl-8,9-dihydrocaffeines 2 and 3 together with unreduced 8-acylcaffeines 4 and 8-(α-hydroxy-alkyl)caffeines 6 are produced.Under similar conditions, the reactions of 2-methylpropanal, 2-methylbutanal and 2,2-dimethylbutanal resulted in the formation of the corresponding 8-alkylcaffeines 7. - Key Words: Caffeine / Aldehydes / Photochemistry / Purines
