581-50-0Relevant articles and documents
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Mukhamedzhanov et al.
, (1968)
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Goshaev et al.
, (1971)
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Continuous Flow as Enabling Technology: Synthesis of Heteroaromatic Sulfinates as Bench Stable Cross-Coupling Partners
Lima, Fabio,André, Jér?me,Marziale, Alexander,Greb, Andreas,Glowienke, Susanne,Meisenbach, Mark,Schenkel, Berthold,Martin, Benjamin,Sedelmeier, Joerg
, p. 6082 - 6085 (2020)
An enabling continuous flow setup for handling of unstable organolithium intermediates and synthesis of heteroaryl sulfinates on a multigram scale is described. The developed continuous flow process allows for the synthesis and simple isolation of heteroaryl sulfinates which are otherwise challenging to access in classical batch mode. The lithium sulfinate salts prepared by this method were shown to be efficient reaction partners in palladium catalyzed C(sp2)-C(sp2) cross-coupling to access medicinally relevant bis-heteroaryl motifs.
Nicotine-related alkaloids and metabolites as inhibitors of human cytochrome P-450 2A6
Denton, Travis T.,Zhang, Xiaodong,Cashman, John R.
, p. 751 - 756 (2004)
S-(-)-Nicotine and 13 of the most prevalent nicotine-related alkaloids and metabolites (i.e., S-(-)-nornicotine, myosmine, β-nicotyrine, S-cotinine, S-norcotinine, S-(-)-nicotine N-1′-oxide, S-(-)-nicotine Δ 1′-5′-iminium ion, S-(-)-anabasine,
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Smith
, p. 959 (1935)
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Ligand-to-metal charge transfer of a pyridine surface complex on TiO2for selective dehydrogenative cross-coupling with benzene
Hishitani, Shinichiro,Naniwa, Shimpei,Yamamoto, Akira,Yoshida, Hisao
, p. 11366 - 11373 (2021/05/31)
Dehydrogenative cross-coupling (DCC) between pyridine and benzene proceeded selectively using a TiO2 photocatalyst under visible light irradiation at optimized concentrations of the substrates. Visible light induces ligand-to-metal charge transfer (LMCT) between pyridine and a TiO2 surface to give a pyridine radical cation, which produces a pyridyl radical by its deprotonation or oxidation of another pyridine molecule. The pyridyl radical attacks a benzene ring to form an sp2C-sp2C bond and a hydrogen atom is subsequently removed to complete DCC. Selective excitation of the pyridine LMCT complex in the presence of an excess amount of benzene would be the key for higher selectivity. This journal is
Synthesis of Pyridylsulfonium Salts and Their Application in the Formation of Functionalized Bipyridines
Duong, Vincent K.,Horan, Alexandra M.,McGarrigle, Eoghan M.
, p. 8451 - 8457 (2020/11/12)
An S-selective arylation of pyridylsulfides with good functional group tolerance was developed. To demonstrate synthetic utility, the resulting pyridylsulfonium salts were used in a scalable transition-metal-free coupling protocol, yielding functionalized bipyridines with extensive functional group tolerance. This modular methodology permits selective introduction of functional groups from commercially available pyridyl halides, furnishing symmetrical and unsymmetrical 2,2′- A nd 2,3′-bipyridines. Iterative application of the methodology enabled the synthesis of a functionalized terpyridine with three different pyridine components.
