174150-58-4Relevant articles and documents
Photoenzymatic Hydrogenation of Heteroaromatic Olefins Using ‘Ene’-Reductases with Photoredox Catalysts
Biegasiewicz, Kyle F.,Black, Michael J.,Chung, Megan M.,Hyster, Todd K.,Meichan, Andrew J.,Nakano, Yuji,Sandoval, Braddock A.,Zhu, Tianyu
supporting information, p. 10484 - 10488 (2020/04/29)
Flavin-dependent ‘ene’-reductases (EREDs) are highly selective catalysts for the asymmetric reduction of activated alkenes. This function is, however, limited to enones, enoates, and nitroalkenes using the native hydride transfer mechanism. Here we demonstrate that EREDs can reduce vinyl pyridines when irradiated with visible light in the presence of a photoredox catalyst. Experimental evidence suggests the reaction proceeds via a radical mechanism where the vinyl pyridine is reduced to the corresponding neutral benzylic radical in solution. DFT calculations reveal this radical to be “dynamically stable”, suggesting it is sufficiently long-lived to diffuse into the enzyme active site for stereoselective hydrogen atom transfer. This reduction mechanism is distinct from the native one, highlighting the opportunity to expand the synthetic capabilities of existing enzyme platforms by exploiting new mechanistic models.
Carbonylative Hiyama coupling of aryl halides with arylsilanes under balloon pressure of CO
Chang, Sheng,Jin, Ying,Zhang, Xiu Rong,Sun, Yong Bing
supporting information, p. 2017 - 2020 (2016/04/26)
An efficient protocol has been developed for the carbonylative Hiyama coupling of aryl halides using the cesium fluoride as a promoter by palladium-catalyzed in NMP. This protocol was applied to a wide variety of functionalized and hindered aryl iodides and bromides with arylsilanes, to afford the desired biaryl ketones in good to excellent yields.
Regioselective functionalization of the oxazole scaffold using TMP-bases of Mg and Zn
Haas, Diana,Mosrin, Marc,Knochel, Paul
supporting information, p. 6162 - 6165 (2014/01/17)
A general method for the synthesis of 2,4,5-trisubstituted oxazoles has been developed. Starting from commercially available oxazole, successive metalations using TMPMgCl·LiCl or TMPZnCl·LiCl led to the corresponding magnesiated or zincated species which
