80360-35-6Relevant academic research and scientific papers
Ligand-Accelerated Iron Photocatalysis Enabling Decarboxylative Alkylation of Heteroarenes
Li, Zhenlong,Wang, Xiaofei,Xia, Siqi,Jin, Jian
supporting information, (2019/06/13)
A mild, practical protocol for the decarboxylative alkylation of heteroarenes has been accomplished via iron photocatalysis. A diverse range of carboxylic acids readily undergo oxidative decarboxylation and then couple with a broad array of heteroarenes in this transformation. The photoexcited state lifetimes of iron complexes are typically much shorter than those of iridium and ruthenium complexes. Here we describe our effort on iron photocatalysis by utilizing the intramolecular charge transfer pathway of iron-carboxylate complexes.
Base-promoted, deborylative secondary alkylation of N-heteroaromatic: N -oxides with internal gem -bis[(pinacolato)boryl]alkanes: A facile derivatization of 2,2′-bipyridyl analogues
Hwang, Chiwon,Jo, Woohyun,Cho, Seung Hwan
supporting information, p. 7573 - 7576 (2017/07/12)
A base-promoted, secondary alkylation of N-heteroaromatic N-oxides using internal gem-bis[(pinacolato)boryl]alkanes as alkylation reagents is reported. The reaction exhibits a broad scope, providing deoxygenated secondary alkylated N-heteroaromatic compounds with high efficiency. The usefulness of the developed protocol is evidenced by the sequential direct alkylation of 2,2′-bipyridine-N-oxide.
Unprotected Amino Acids as Stable Radical Precursors for Heterocycle C-H Functionalization
Mai, Duy N.,Baxter, Ryan D.
supporting information, p. 3738 - 3741 (2016/08/16)
An efficient and general method for the C-H alkylation of heteroarenes using unprotected amino acids as stable alkyl radical precursors is reported. This one-pot procedure is performed open to air under aqueous conditions and is effective for several natural and unnatural amino acids. Heterocycles of varying structure are suitably functionalized, and reactivity trends reflect the nucleophilic character of the radical species generated.
AgNO2-mediated direct nitration of the quinoxaline tertiary benzylic C-H bond and direct conversion of 2-methyl quinoxalines into related nitriles
Wu, Degui,Zhang, Jian,Cui, Jianhai,Zhang, Wei,Liu, Yunkui
supporting information, p. 10857 - 10860 (2014/09/30)
A unique method for AgNO2-mediated direct nitration of the quinoxaline tertiary C-H bond and direct conversion of 2-methyl quinoxalines into 2-quinoxaline nitriles under oxidative conditions has been developed. This protocol provides an efficient way to access quinoxaline containing nitroalkanes and nitriles depending on different substrate selection. the Partner Organisations 2014.
Highly selective palladium-catalyzed cross-coupling of secondary alkylzinc reagents with heteroaryl halides
Yang, Yang,Niedermann, Katrin,Han, Chong,Buchwald, Stephen L.
supporting information, p. 4638 - 4641 (2015/01/08)
The highly selective palladium-catalyzed Negishi coupling of secondary alkylzinc reagents with heteroaryl halides is described. The development of a series of biarylphosphine ligands has led to the identification of an improved catalyst for the coupling of electron-deficient heterocyclic substrates. Preparation and characterization of oxidative addition complex (L)(Ar)PdBr provided insight into the unique reactivity of catalysts based on CPhos-type ligands in facilitating challenging reductive elimination processes.
Polar effects in free-radical reactions. A novel homolytic acylation of heteroaromatic bases by aerobic oxidation of aldehydes, catalysed by N-hydroxyphthalimide and Co salts
Minisci, Francesco,Recupero, Francesco,Cecchetto, Andrea,Punta, Carlo,Gambarotti, Cristian,Fontana, Francesca,Pedulli, Gian Franco
, p. 325 - 328 (2007/10/03)
A new process for the homolytic acylation of protonated heteroaromatic bases is described; an N-oxyl radical (PINO) generated from N-hydroxyphthalimide by air oxygen and Co(II) abstracts a hydrogen atom from an aldehyde. The resulting nucleophilic acyl radical adds to a heteroaromatic base, which is then rearomatised in a chain process. Quinazoline has an anomalous behaviour, giving 3H-quinazolin-4-one as the only reaction product.
New General Processes of Homolytic Alkylation of Heteroaromatic Bases by t-BuOOH or (t-BuO)2 and Alkyl Iodides
Fontana, Francesca,Minisci, Francesco,Barbosa, Maria Claudia Nogueira,Vismara, Elena
, p. 995 - 999 (2007/10/02)
New general, selective processes of homolytic alkylation of protonated heteroaromatic bases have been developed using alkyl iodides and t-BuOOH or (t-BuO)2 as sources of alkyl radicals.Both processes are based on the generation of methyl radical from the peroxides, and on iodine abstraction from the alkyl iodide by the methyl radical.The selective processes are the result of combined enthalpic and polar effects.The enthalpic factor governs the equilibrium of iodine abstraction, whereas the polar effect governs the reactivity of the alkyl radicals with the protonated heteroaromatic ring.A redox chain is operative with t-BuOOH and an unusual free-radical chain process is involved with (t-BuO)2.Both chains are particularly effective because of the electron-transfer oxidation of the pyridyl radical intermediate, the ionization potential of which (5.4-6.0 eV) is close to that of lithium (5.39 eV) or sodium (5.14 eV).
SRN1 Mechanism in Heteroaromatic Nucleophilic Substitution. Reactions of 2-Chloroquinoxaline and 4-Chloroquinazolines with Ketone Enolates
Carver, David R.,Hubbard, James S.,Wolfe, James F.
, p. 1036 - 1040 (2007/10/02)
Reaction of 2-chloroquinoxaline (1) with O-potassio-3,3-dimethyl-2-butanone (2) in liquid NH3 affords 1-(quinoxalin-2-yl)-3,3-dimethyl-2-butanone (3) via a thermal SRN1 mechanism and 2-tert-butylfuroquinoxaline (4) via a competing ionic,
