5894-65-5Relevant academic research and scientific papers
FTIR investigation of solvent effects of N-methyl and N-tert-butyl benzamide
Jovi,Nikoli,Petrovi,Kordi,Crossed D Signakovi-Sekuli,Stojanovi
, p. 1616 - 1622 (2014)
Infrared spectroscopy studies of N-methyl benzamide and N-tert-butyl benzamide in 12 organic solvents were undretaken to investigate solvent-solute interactions. The wavenumbers of carbonyl stretching vibration ν(C=O) in different solvents were correlated
The Thermal Decomposition of N,O-Diacyl-N-t-butylhydroxylamines. IV. A Novel Acyloxyl Migration in N,O-Diacyl-N-t-butylhydroxylamines
Uchida, Yuzuru,Kozuka, Seizi
, p. 2681 - 2682 (1982)
Several N,O-diacyl-N-t-butylhydroxylamines were prepared, and their thermal decompositions were studied.N-Propionyl-O-benzoyl-N-t-butylhydroxylamine gave N-t-butyl-2-benzoyloxypropanamide, together with the decomposition products, N-t-butylpropanamide and benzoic acid, upon thermal decomposition in tetralin.Similar benzyloxyl migrations were found in the thermal decomposition of N-butyryl, N-valeryl, and N-(3-phenylpropionyl) derivatives.
Reactions of (E)-2-tert-Butyl-3-phenyloxaziridine with Lithium Amide
Newcomb, Martin,Reeder, Robert A.
, p. 1489 - 1493 (1980)
The reactions of (E)-2-tert-butyl-3-phenyloxaziridine (1a) with lithium amide bases in tetrahydrofuran have been studied.In competing rections, 1a is reduced to N-tert-butylbenzaldimine (2) and isomerized to N-tert-butylbenzamide (3).The former reaction proceeds through an intermediate which accumulates and slowly decomposes to 2; the reaction apparently occurs via an initial electron transfer from the base to the oxaziridine.The latter reaction occurs by simultaneous deprotonation and ring opening of the oxaziridine to give the anion of 3.
Borrowing and Returning Oxygen Atom in Trifluoroacetic Anhydride Transfer to Nitrones: A Versatile Route for the Synthesis of N-Trifluoroacetyl Amides
Wang, Junwen,Weng, Zhiqiang
, p. 1330 - 1334 (2019)
A method for the synthesis of N-trifluoroacetyl amides through trifluoroacetic anhydride transfer to nitrones by borrowing and returning oxygen atom is reported. The reaction appears to proceed via electrophilic trifluoroacetylation, followed by nucleophi
AMINE-BORANES AS BIFUNCTIONAL REAGENTS FOR DIRECT AMIDATION OF CARBOXYLIC ACIDS
-
Paragraph 0008-0009; 0063-0064, (2022/03/04)
The present invention generally relates to a process for selective and direct activation and subsequent amidation of aliphatic and aromatic carboxylic acids to afford an amide R3CONR1R2. That the process is capable of delivering gaseous or low-boiling point amines provides a major advantage over existing methodologies, which involves an intermediate of triacyloxyborane-amine complex [(R3CO2)3—B—NHR1R2]. This procedure readily produces primary, secondary, and tertiary amides, and is compatible with the chirality of the acid and amine involved. The preparation of known pharmaceutical molecules and intermediates has also been demonstrated.
Remarkably Efficient Iridium Catalysts for Directed C(sp2)-H and C(sp3)-H Borylation of Diverse Classes of Substrates
Chattopadhyay, Buddhadeb,Hassan, Mirja Md Mahamudul,Hoque, Md Emdadul
, p. 5022 - 5037 (2021/05/04)
Here we describe the discovery of a new class of C-H borylation catalysts and their use for regioselective C-H borylation of aromatic, heteroaromatic, and aliphatic systems. The new catalysts have Ir-C(thienyl) or Ir-C(furyl) anionic ligands instead of the diamine-type neutral chelating ligands used in the standard C-H borylation conditions. It is reported that the employment of these newly discovered catalysts show excellent reactivity and ortho-selectivity for diverse classes of aromatic substrates with high isolated yields. Moreover, the catalysts proved to be efficient for a wide number of aliphatic substrates for selective C(sp3)-H bond borylations. Heterocyclic molecules are selectively borylated using the inherently elevated reactivity of the C-H bonds. A number of late-stage C-H functionalization have been described using the same catalysts. Furthermore, we show that one of the catalysts could be used even in open air for the C(sp2)-H and C(sp3)-H borylations enabling the method more general. Preliminary mechanistic studies suggest that the active catalytic intermediate is the Ir(bis)boryl complex, and the attached ligand acts as bidentate ligand. Collectively, this study underlines the discovery of new class of C-H borylation catalysts that should find wide application in the context of C-H functionalization chemistry.
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.
supporting information, 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.
Insight into Regioselective Control in Aerobic Oxidative C-H/C-H Coupling for C3-Arylation of Benzothiophenes: Toward Structurally Nontraditional OLED Materials
Bin, Zhengyang,Liao, Xingrong,Liu, Jiahui,Shen, Boming,Shi, Yang,Yan, Lipeng,Yang, Feng,Yang, Ge,Yang, Yudong,You, Jingsong,Yu, Peiyuan
supporting information, (2021/12/14)
The installation of (benzo)thiophene-containing biaryls via coupling reactions has become a staple in designing photoelectric materials. Undeniably, C-H/C-H cross-coupling reactions between two (hetero)aromatics would be a shortcut toward these structural fragments. While more reliable cross-coupling technologies are well-established to provide C2-arylated (benzo)thiophenes, efficient methods that arylate the C3-position remain underdeveloped. Herein we provide insight into the factors that determine regioselectivity switching for these cross-coupling reactions. X-ray crystallographic analysis gives solid evidence for the key roles of triflate in regioselective dearomatization and acetate in base-assisted anti-β-deprotonated rearomatization. The first isolation and X-ray characterization of a medium-sized dearomatized cyclometalated adduct involving both substrates provide extra insight into aerobic oxidative Ar-H/Ar-H cross-coupling reactions. The mechanistic breakthrough incubates the first example, enabling C-H/C-H-type C3-arylation of benzothiophenes. Finally, this chemistry is used to design blue-emitting thermally activated delayed fluorescence (TADF) materials with a helicene conformation that exhibit a high maximum external quantum efficiency of 25.4% in OLED.
NaOTs-promoted transition metal-free C-N bond cleavage to form C-X (X = N, O, S) bonds
Chen, Wei,Liu, Sicheng,Liu, Tingting,Majeed, Irfan,Ye, Xiaojing,Zeng, Zhuo,Zhang, Yuqi,Zhu, Yulin
supporting information, p. 8566 - 8571 (2021/10/20)
Multifunctional transformation of amide C-N bond cleavage is reported. The protocol applies to benzamide, thioamide, alcohols, and mercaptan under similar reaction conditions catalyzed by NaOTs. It is noteworthy that NaOTs can not only be recycled and reused for up to three cycles without significant loss in catalytic activity, but also catalyze gram-grade reactions. This study provides a novel solution with mild conditions and a simple procedure for transformation of multiple amides.
Weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis
Park, Jin,Park, Sehoon,Jang, Gwang Seok,Kim, Ran Hui,Jung, Jaehoon,Woo, Sang Kook
supporting information, p. 9995 - 9998 (2021/10/06)
The selective rearrangement of oxaziridines to amidesviaa single electron transfer (SET) pathway is unexplored. In this study, we present a weak base-promoted selective rearrangement of oxaziridines to amidesviavisible-light photoredox catalysis. The developed method shows excellent functional group tolerance with a broad substrate scope and good to excellent yields. Furthermore, control experiments and density functional theory (DFT) calculations are performed to gain insight into the reactivity and selectivity.
