14599-03-2Relevant articles and documents
Photochemical Activation of Aromatic Aldehydes: Synthesis of Amides, Hydroxamic Acids and Esters
Nikitas, Nikolaos F.,Apostolopoulou, Mary K.,Skolia, Elpida,Tsoukaki, Anna,Kokotos, Christoforos G.
, p. 7915 - 7922 (2021/05/03)
A cheap, facile and metal-free photochemical protocol for the activation of aromatic aldehydes has been developed. Utilizing thioxanthen-9-one as the photocatalyst and cheap household lamps as the light source, a variety of aromatic aldehydes have been activated and subsequently converted in a one-pot reaction into amides, hydroxamic acids and esters in good to high yields. The applicability of this method was highlighted in the synthesis of Moclobemide, a drug against depression and social anxiety. Extended and detailed mechanistic studies have been conducted, in order to determine a plausible mechanism for the reaction.
3,6-Di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed metal-free amide bond formation from thioacids and amines at room temperature
Samanta, Suvendu,Ray, Shounak,Bhaduri, Samanka Narayan,Samanta, Partha Kumar,Biswas, Papu
supporting information, (2020/08/10)
A 3,6-di(pyridin-2-yl)-1,2,4,5-tetrazine (pytz) catalysed efficient, mild and metal-free method has been developed for direct amide bond synthesis from simple thioacids and amines as starting materials. This methodology is useful for aromatic, aliphatic, and heteroaromatic thioacids as well as primary, secondary, heterocyclic, and even functionalized amines. A wide substrates scope, operationally mild conditions, and acylation of amines without affecting other functional groups such as alcohols, esters, carbodithioates, among others make this strategy very attractive and practical.
Hydrogen Bond Directed ortho-Selective C?H Borylation of Secondary Aromatic Amides
Bai, Shao-Tao,Bheeter, Charles B.,Reek, Joost N. H.
supporting information, p. 13039 - 13043 (2019/07/31)
Reported is an iridium catalyst for ortho-selective C?H borylation of challenging secondary aromatic amide substrates, and the regioselectivity is controlled by hydrogen-bond interactions. The BAIPy-Ir catalyst forms three hydrogen bonds with the substrate during the crucial activation step, and allows ortho-C?H borylation with high selectivity. The catalyst displays unprecedented ortho selectivities for a wide variety of substrates that differ in electronic and steric properties, and the catalyst tolerates various functional groups. The regioselective C?H borylation catalyst is readily accessible and converts substrates on gram scale with high selectivity and conversion.
