19486-73-8Relevant academic research and scientific papers
Thermolysis of 2-diazo-3-aryl ketoesters: New route to α-aryl malonates and aromatic esters
Zhang, Zhao,Tang, Mengyao,Zang, Lei,Zou, Liang-Hua,Li, Jie
, p. 5681 - 5684 (2016)
Thermochemical excitation enabled efficient α-aryl malonates synthesis from 2-diazo-3-aryl ketoesters and alcohols under transition metal-free reaction conditions. Furthermore, an unusual C[sbnd]C bond cleavage and C[sbnd]O/(N) bond formation occurred whe
One-pot sequential Schmidt and Ritter reactions for the synthesis of N-tert-butyl amides
Hazarika, Nabajyoti,Baishya, Gakul
, p. 5686 - 5690 (2014)
The first example of the direct conversion of benzaldehydes into their corresponding N-tert-butyl amides through a Schmidt reaction/Ritter reaction sequence is described. A reagent mixture consisting of NaN3 and HBF4?OEt2 in acetic acid efficiently reacts with aromatic and conjugated (α,β-unsaturated) aldehydes to produce nitrile derivatives, which in situ undergo a Ritter reaction with tert-butyl acetate to afford the corresponding N-tert-butyl amides in almost quantitative yields. The method needs no column chromatography purification. The wide substrate scope as well as the ready availability of the reagent system also make this protocol convenient.
Mechanistic insights and safety evaluation of the Ritter reaction utilizing tert -butyl acetate as the tert -butyl cation source
Roberts, Scott W.,Shaw, Stephen M.,Milne, Jacqueline E.,Cohen, Dawn E.,Tvetan, Justin T.,Tomaskevitch, Joseph,Thiel, Oliver R.
, p. 2058 - 2063 (2012)
The Ritter reaction utilizing tert-butyl acetate as the tert-butyl cation source was investigated by in situ FTIR and calorimetry under various reaction conditions. It was established that, when a batch mode reaction in acetic acid was performed, minimal isobutylene was evolved into the headspace, thereby avoiding pressurization of the reaction vessel. The safety of these conditions is due to the equilibrium of isobutylene and acetic acid with tert-butyl acetate. In addition, the observation of acetic anhydride provided insight into the role of acetic acid in the mechanistic pathway.
Method for synthesizing amide by using methyl arene and amine in water phase
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Paragraph 0015; 0061-0064, (2021/03/06)
The invention provides a high-efficient method of synthesizing amide with methyl aromatics and amine. In the method, with the methyl aromatics and the amine as the raw materials in the water phase and TBHP and TBAI respectively as an oxidizing agent and a catalyst, a sp3 C-H bond and a sp3 N-H bond are broken and a C-N bond is formed. Compared with a conventional method of synthesizing the amide from oxidized amide, in which an activated acyl group or amine is required, the method is carried out with water as the solvent so that the method is not only economical but also environmental-protective. The method has a very good application prospect in the field of synthesizing polypeptide, protein and drugs in future.
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.
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.
Catalyst-free synthesis of phenanthridinesviaelectrochemical coupling of 2-isocyanobiphenyls and amines
Malviya, Bhanwar Kumar,Singh, Karandeep,Jaiswal, Pradeep K.,Karnatak, Manvika,Verma, Ved Prakash,Badsara, Satpal Singh,Sharma, Siddharth
, p. 6367 - 6378 (2021/04/16)
Catalyst free synthesis of 6-aryl phenanthridines and amides through an electrochemical reaction is reported in this study. The coupling reaction proceeds by the cathodic reduction ofin situformed diazonium ions, which are formed from anilines and an alkyl nitrite. The generated aryl radical diazonium ions coupled from isocyanides furnished the desired products in good yields. This cascade reaction was conducted in an undivided cell equipped with an RVC as the anode and Pt as the cathode usingnBu4NBF4as the electrolyte at room temperature. A series of detailed mechanistic studies have also been performed, including a radical clock experiment and cyclic voltammetry analysis.
A case study of Pd?Pd intramolecular interaction in a benzothiazole based palladacycle; catalytic activity toward amide synthesisviaan isocyanide insertion pathway
Loni, Masood,Balmohammadi, Yaser,Dadgar Yeganeh, Reza,Imani, Kaveh,Notash, Behrouz,Bazgir, Ayoob
supporting information, p. 3290 - 3297 (2021/02/26)
An acetate bridge benzothiazolepalladacycle containing a rare metallophilic intramolecular Pd?Pd interaction was synthesized and thoroughly characterized. The synthesized benzothiazolepalladacycle directly anchored on SBA-15 to form an efficient heterogen
Quinolin-8-yl Formate: A New Option for Small-Scale Carbonylation Reactions in Microwave Reactors
Maddocks, Christopher J.,Aathimanikandan, Sivakumar V.,Richardson, Jeffery,Ruble, J. Craig
, p. 1608 - 1612 (2020/09/09)
A convenient procedure for conducting small-scale carbonylations of aryl or benzyl halides in a microwave reactor by using quinolin-8-yl formate is described. The resulting 8-acyloxyquinolines were shown to be more reactive than phenyl esters in acyl-tran
Ionic liquid catalyzed Ritter reaction/Pd-catalyzed directed Ortho-arylation; facile access to diverse libraries of biaryl-amides from Aryl-nitriles
Sutar, Suraj M.,Savanur, Hemantkumar M.,Kalkhambkar, Rajesh G.,Borosky, Gabriela L.,Aridoss, Gopalakrishnan,Laali, Kenneth K.
supporting information, (2020/10/30)
Diverse libraries of biaryl-amides bearing N-t-butyl and N-adamantyl groups were synthesized in two steps by the Ritter reaction of aryl-nitriles, using tBuOH and AdaOH as carbocation precursors, and employing [BMIM(SO3H)][OTf] (neat or with [B
