14028-67-2Relevant academic research and scientific papers
Environmentally benign decarboxylative: N-, O-, and S-Acetylations and acylations
Ghosh, Santanu,Purkait, Anisha,Jana, Chandan K.
supporting information, p. 8721 - 8727 (2020/12/30)
An operationally simple and general method for acetylation and acylation of a wide variety of substrates (amines, alcohols, phenols, thiols, and hydrazones) has been reported. Meldrum's acid and its derivatives have been used as an air-stable, non-volatile, cost-effective, and easy to handle acetylating/acylating agent. Easily separable byproducts (CO2 and acetone) allowed the isolation of analytically pure acetylated products without the requirement of work-up and any chromatography. This journal is
Aerobic α-Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones via Organo-photocatalysis
Aganda, Kim Christopher C.,Hong, Boseok,Lee, Anna
supporting information, p. 1124 - 1129 (2019/01/25)
An efficient visible-light-induced α-oxidation of N-substituted tetrahydroisoquinolines to dihydroisoquinolones has been developed using eosin Y as an organo-photocatalyst and oxygen as a green oxidant. The reactions were carried out under mild reaction conditions; the desired dihydroisoquinolones were obtained in up to 96% yield at room temperature under oxygen atmosphere. This transformation provides a convenient route to dihydroisoquinolones with a wide range of substrates. (Figure presented.).
Carbonylation of C?N Bonds in Tertiary Amines Catalyzed by Low-Valent Iron Catalysts
Nasr Allah, Tawfiq,Savourey, Solène,Berthet, Jean-Claude,Nicolas, Emmanuel,Cantat, Thibault
supporting information, p. 10884 - 10887 (2019/07/15)
The first iron catalysts able to promote the formal insertion of CO into the C?N bond of amines are reported. Using low-valent iron complexes, including K2[Fe(CO)4], amides are formed from aromatic and aliphatic amines, in the presence of an iodoalkane promoter. Inorganic Lewis acids, such as AlCl3 and Nd(OTf)3, have a positive influence on the catalytic activity of the iron salts, enabling the carbonylation at a low pressure of CO (6 to 8 bars).
Regioselectivity Control in the Oxidative Formal [3 + 2] Annulations of Ketoxime Acetates and Tetrohydroisoquinolines
Qu, Zhonghua,Zhang, Feng,Deng, Guo-Jun,Huang, Huawen
, p. 8239 - 8243 (2019/10/16)
A novel copper-catalyzed oxidative formal [3 + 2] annulations of ketoxime acetates and tetrohydroisoquinolines for the synthesis of fused pyrazoles and imidazoles has been developed. A broad range of important isoquinoline-fused pyrazole and imidazole pro
Synthesis of acetamides using CO2, methanol, H2 and amines
Zhang, Jingjing,Qian, Qingli,Wang, Ying,Asare Bediako, Bernard Baffour,Cui, Meng,Yang, Guanying,Han, Buxing
supporting information, p. 233 - 237 (2019/01/28)
Herein, we report the synthesis of acetamides from CO2, methanol, H2 and corresponding amines, which is a new route used to synthesize acetamides. It was found that the Rh catalyst with LiI/LiCl as promoters could effectively catalyze this reaction. Interestingly, no ligand was required and amine substrates played a role in accelerating the reaction.
Mn(II)-Catalyzed N -Acylation of Amines
Ma, Juan,Zhang, Jingyu,Gong, Hang
, p. 693 - 703 (2019/01/23)
A practical protocol has been developed here for the Mn(II)-catalyzed N -acylation of amines with high yields using N, N -dimethylformamide and other amides as the carbonyl source. The protocol is simple, does not require any acid, base, ligand, or other additives, and encompasses a broad substrate scope for primary, secondary, and heterocyclic amines.
Visible light mediated oxidation of benzylic sp3 C-H bonds using catalytic 1,4-hydroquinone, or its biorenewable glucoside, arbutin, as a pre-oxidant
Finney, Laura C.,Mitchell, Lorna J.,Moody, Christopher J.
supporting information, p. 2242 - 2249 (2018/05/28)
Benzylic ethers undergo a visible light induced C-H activation and oxygen insertion to give the corresponding benzoate esters in moderate to good yields. The conditions employ substoichiometric amounts of 1,4-hydroquinone with copper(ii) chloride dihydrate as an electron-transfer mediator, oxygen as the terminal oxidant and dimethyl carbonate as solvent under visible light irradiation. The naturally occurring glucoside, arbutin, which is commercially available or can be accessed via extraction of the leaves of bearberry (Arctostaphylos uva-ursi) or elephant ears (Bergenia crassifolia) can be used as a biorenewable source of 1,4-hydroquinone. The methodology exploits the increase in oxidizing ability of quinones upon irradiation with visible light, and offers a sustainable alternative for the late stage oxidative functionalization of benzylic C-H bonds. It is applicable to a range of cyclic benzylic ethers such as isochromans and phthalans, and simple benzyl alkyl ethers. It can also be applied in the oxidation of benzylic amines into amides, and of diarylmethanes into the corresponding ketones. Mechanistic studies suggest that the reaction proceeds by H-abstraction by the photo-excited triplet benzoquinone to give a benzylic radical that subsequently reacts with molecular oxygen.
Cobalt(II)-Catalyzed N-Acylation of Amines through a Transamidation Reaction
Ma, Juan,Zhang, Feng,Zhang, Jingyu,Gong, Hang
, p. 4940 - 4948 (2018/09/25)
A practical protocol has been developed for a Co(OAc)2·4H2O-catalyzed transamidation reaction. The reaction gives high yields and uses N,N-dimethylformamide and other amides as carbonyl sources. The protocol is rapid and simple, and it does not require any acids, bases, ligands, or other additives. It works well for a wide range of primary, secondary, and heterocyclic amines.
N-formylation of amine using graphene oxide as a sole recyclable metal-free carbocatalyst
Ma, Juan,Zhang, Jingyu,Zhou, Xiao,Wang, Jiawei,Gong, Hang
, p. 2851 - 2860 (2018/10/31)
Abstract: Graphene oxide (GO), an inexpensive, environment-friendly, and metal-free carbocatalyst, used for the N-formylation of amines is developed. In this reaction, GO shows good activity, selectivity, and recyclability. This strategy has an array of advantages, such as being metal free, without additive, wide-scope protocol, scalable with a low catalyst loading of 3?wt%, use of readily available and recyclable carbocatalyst, and DMF as a readily available formyl source. Furthermore, this strategy provides an avenue for the convenient hydroformylation of various amines. Graphical abstract: [Figure not available: see fulltext.].
N-Aryl Groups Are Ubiquitous in Cross-Dehydrogenative Couplings Because They Stabilize Reactive Intermediates
Tsang, Althea S.-K.,Hashmi, A. Stephen K.,Comba, Peter,Kerscher, Marion,Chan, Bun,Todd, Matthew H.
supporting information, p. 9313 - 9318 (2017/07/17)
The mechanism of cross-dehydrogenative coupling (CDC) reactions has been examined by experimental and computational methods. We provide a rationale for the ubiquity of the N-aryl group in these reactions. The aryl substituent stabilizes two intermediates
