36475-51-1Relevant academic research and scientific papers
Identifying the potential of pulsed LED irradiation in synthesis: Copper-photocatalysed C-F functionalisation
Nicholls, Thomas P.,Robertson, Johnathon C.,Gardiner, Michael G.,Bissember, Alex C.
supporting information, p. 4589 - 4592 (2018/05/14)
It has been reported that pulsed irradiation can improve photosynthetic activity and phytochemical production in plants. Intrigued and inspired by these observations, we postulated that pulsed irradiation strategies may have broader implications in organic synthesis. We report here the results of a proof-of-concept study demonstrating that pulsed LED irradiation enhances the efficiency of a visible light-mediated photoredox-catalysed reaction. The design and construction of an inexpensive multiphase circuit (～US$5) enabling power and pulse frequency modulation, which is connected to light-emitting diodes (LEDs), provides a source of pulsed visible light. This technology was then utilised to establish a novel copper-photocatalysed dual α-amino C-H/C-F functionalisation reaction. Pulsed blue LED irradiation was shown to be crucial for facilitating a much more efficient process and increasing the rate of product formation. Our results suggest that pulsed irradiation strategies have the potential to contribute to enhancing the synthetic utility and extending the scope of first row transition metal-based photoredox catalysts. We also anticipate that this approach will find wider applications in synthesis.
Room-temperature amination of deactivated aniline and aryl halide partners with carbonate base using a Pd-PEPPSI-IPentCl-o-picoline catalyst
Pompeo, Matthew,Farmer, Jennifer L.,Froese, Robert D. J.,Organ, Michael G.
supporting information, p. 3223 - 3226 (2014/04/03)
Current state-of-the-art protocols for the coupling of unreactive amines (e.g., electron-poor anilines) with deactivated oxidative-addition partners (e.g., electron-rich and/or hindered aryl chlorides) involve strong heating (usually >100 °C) and/or tert-butoxide base, and even then not all couplings are successful. The aggressive base tert-butoxide reacts with and in many instances destroys the typical functional groups that are necessary for the function of most organic molecules, such as carbonyl groups, esters, nitriles, amides, alcohols, and amines. The new catalyst described herein, Pd-PEPPSI-IPentCl-o-picoline, is able to aminate profoundly deactivated coupling partners when using only carbonate base at room temperature. Running mild: An N-heterocyclic carbene complex of palladium (1) was systematically designed to enable the amination of strongly deactivated substrates (R1 can be strongly electron donating, R2 can be strongly electron-withdrawing) when using the most mild of bases (carbonate) at room temperature. This catalyst was used to produce elaborate, richly functionalized products for use in life-, health-, and material-science applications.
Copper(II) acetate catalyzed cross-coupling of pentafluorophenylboronic acid with amines under an atmosphere of oxygen
Zhong, Weihui,Liu, Zhenyu,Yu, Chuanming,Su, Weike
experimental part, p. 2888 - 2892 (2009/05/07)
Under an atmosphere of oxygen and a catalytic amount of Cu(OAc) 2, pentafluorophenylboronic acid reacted with anilines at room temperature to produce the corresponding N-pentafluorophenylanilines in moderate to good yields. In the case of alkylamines, unexpected N-alkyl-2,2′,3, 3′,4′,5,5′,6,6′-nona-fluorobiphenyl-4-amines were formed under the similar conditions in moderate yields. Georg Thieme Verlag Stuttgart.
