14 research outputs found
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Continuous-Flow Synthesis and Derivatization of Aziridines through Palladium-Catalyzed C(sp 3 )âH Activation
A continuousâflow synthesis of aziridines by palladiumâcatalyzed C(sp3)âH activation is described. The new flow reaction could be combined with an aziridineâringâopening reaction to give highly functionalized aliphatic amines through a consecutive process. A predictive mechanistic model was developed and used to design the CâH activation flow process and illustrates an approach towards firstâprinciples design based on novel catalytic reactions.We are grateful to the Department of Chemical Engineering and Biotechnology (J.Z.) and the EPSRC (A.P.S.) for studentships, and to the ERC and EPSRC (EP/100548X/1) for fellowships (M.J.G.). Mass spectroscopy data were acquired at the EPSRC UK National Mass Spectroscopy Facility at Swansea Universit
Continuous direct anodic flow oxidation of aromatic hydrocarbons to benzyl amides
No oxidant needed â just electric current! Continuous synthesis of benzyl amides directly from aromatic hydrocarbons.</p
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Combination of Enabling Technologies to Improve and Describe the Stereoselectivity of Wolff-Staudinger Cascade Reaction
A new, single-mode bench-top resonator was evaluated for the microwave-assisted flow generation of primary ketenes by thermal decomposition of α-diazoketones at high temperature. A number of amides and ÎČ-lactams were obtained by ketene generation in situ and reaction with amines and imines, respectively, in good to excellent yields. The preferential formation of trans-configured ÎČ-lactams was observed during the [2+2] Staudinger cycloaddition of a range of ketenes with different imines under controlled reaction conditions. Some insights into the mechanism of this reaction at high temperature are reported, and a new web-based molecular viewer, which takes advantage from Augmented Reality (AR) technology, is also described for a faster interpretation of computed data.The authors are also thankful to the EPSRC (Award Nos. EP/K009494/1, EP/K039520/1 and EP/M004120/1) for financial support
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Research data supporting "Continuous direct anodic flow oxidation of aromatic hydrocarbons to benzyl amides"
An efficient continuous method to convert aromatic hydrocarbons directly into the benzyl amides using flow electrochemistry was developed. It was found that the conversion to the amide was higher while in the presence of a BrĂžnsted acid additive and that the electrochemical process was stable over the time (9 h). The scope of the method as well as the functional group tolerance was further investigated
Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes.
A range of heterocycles, namely thiazoles, imidazoles, imidazopyridines, thiazolidines and dimethoxyindoles, have been synthesised directly from alkenes via a two-step ketoidoination/cyclisation protocol. The alkene starting materials are themselves readily accessible using many different and well-established approaches, and allow access to a variety of heterocycles with excellent yields and regioselectivity
Direct Preparation of Heteroaromatic Compounds from Alkenes
A series of aromatic heterocycles, thiazoles, imidazoles, and dimethoxyindoles, can be synthesised directly from alkenes via a ketoiodination-cyclisation protocol. The alkene starting materials are themselves easily accessible by many different and well-established approaches, and allow access to various aromatic heterocycles with excellent yields and regioselectivity. © Georg Thieme Verlag Stuttgart - New York
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Research data supporting [Unveiling the role of boroxines in metal-free carbon-carbon homologations using diazo compounds and boronic acid]
By means of computational and experimental mechanistic studies the fundamental role of boroxines in the
reaction between diazo compounds and boronic acids was elucidated. Consequently, a selective metalfree
carbonâcarbon homologation of aryl and vinyl boroxines using TMSCHN2, giving access to TMSpinacol
boronic ester products, was developed
Visible Light Activation of Boronic Esters Enables Efficient Photoredox C(sp)-C(sp) Cross-Couplings in Flow
We report herein a new method for the photoredox activation of boronic esters. Using these reagents, an efficient and high-throughput continuous flow process was developed to perform a dual iridium- and nickel-catalyzed C(sp)âC(sp) coupling by circumventing solubility issues associated with potassium trifluoroborate salts. Formation of an adduct with a pyridine-derived Lewis base was found to be essential for the photoredox activation of the boronic esters. Based on these results we were able to develop a further simplified visible light mediated C(sp)âC(sp) coupling method using boronic esters and cyano heteroarenes under flow conditions.Novartis Pharma AG, Engineering and Physical Sciences Research Council (Grant IDs: EP/K0099494/1, EP/K039520/1