65241-91-0Relevant academic research and scientific papers
N-Heterocyclic Carbene-Photocatalyzed Tricomponent Regioselective 1,2-Diacylation of Alkenes Illuminates the Mechanistic Details of the Electron Donor-Acceptor Complex-Mediated Radical Relay Processes
Jin, Shengfei,Sui, Xianwei,Haug, Graham C.,Nguyen, Viet D.,Dang, Hang T.,Arman, Hadi D.,Larionov, Oleg V.
, p. 285 - 294 (2022/01/03)
Progress in the development of photocatalytic reactions requires a detailed understanding of the mechanisms underpinning the observed reactivity, yet mechanistic details of many photocatalytic systems, especially those that involve electron donor-acceptor complexes, have remained elusive. We report herein the development and a combined mechanistic and computational study of photocatalytic alkene 1,2-diacylation that enables a regioselective installation of two different acyl groups, establishing direct, tricomponent access to 1,4-diketones, key intermediates in heterocyclic and medicinal chemistry. The studies revealed the central role of the electron donor-acceptor complex formed from an N-heterocyclic carbene (NHC) catalyst-derived intermediate and an acyl transfer reagent, providing a detailed description of the structural and electronic factors determining the characteristics of the photoinduced charge-transfer process that mediates photocatalytic transformation. The in-depth investigation also illuminated the roles of other radical intermediates and electron donors relevant to the catalytic activities of N-heterocyclic carbenes in radical reactions.
Light-Driven Vitamin B12-Catalysed Generation of Acyl Radicals from 2-S-Pyridyl Thioesters
Ociepa, Micha?,Baka, Oskar,Narodowiec, Jakub,Gryko, Dorota
supporting information, p. 3560 - 3565 (2017/10/24)
Acyl radicals are invaluable intermediates in organic synthesis, however their generation remains challenging. Herein, we present an unprecedented light-driven, cobalt-catalysed method for the generation of acyl radicals from readily available 2-S-pyridyl thioesters. The synthetic potential of this methodology was demonstrated in the Giese-type acylation of activated olefins in the presence of heptamethyl cobyrrinate. This vitamin B12 derivative proved to be the most efficient catalyst in the studied process. The developed method features broad substrate scope (38 examples), good functional group tolerance, and mild reaction conditions. Moreover, it is easily scalable (illustrated on a 20-fold scale-up procedure), enabling its preparative use. Mechanistic studies revealed that the reaction proceeds via a radical pathway with the key steps involving the formation of an acyl-vitamin B12 complex and subsequent photolysis of the Co?C bond. (Figure presented.).
Design and synthesis of novel triazole linked pyrrole derivatives as potent Mycobacterium tuberculosis inhibitors
Devi, M. Lakshmi,Reddy, P. Lakshmi,Yogeeswari,Sriram,Reddy, T. Veera,Reddy, B. V. Subba,Narender
, p. 2985 - 2999 (2017/11/03)
This research is focused on the rational approach to design and synthesis of a novel series of triazole linked pyrrole derivatives through a sequential Paal–Knorr reaction and Click chemistry. These new molecules were screened against Mycobacterium tuberculosis H37Rv and found to display promising anti-mycobacterial activity. Among various compounds, 7g and 7l were identified as leads with minimum inhibitory concentration value 0.78 (μg/mL), which are more effective than standard drugs such as pyrazinamide, ethambutol, and ciprofloxacin and less active than isoniazid and rifampicin. These molecules (minimum inhibitory concentration values 12.5 μg/mL) were also screened against HEK-293T cancer cell lines. Most of these molecules are less toxic but possess higher selectivity index, which indicates the suitability of these compounds for further evaluation.
Radical 1,2-Alkylarylation/Acylarylation of Allylic Alcohols with Aldehydes via Neophyl Rearrangement
Pan, Changduo,Ni, Qingting,Fu, Yu,Yu, Jin-Tao
, p. 7683 - 7688 (2017/07/26)
A metal-free 1,2-alkylarylation of allylic alcohols with aliphatic aldehydes through concomitant radical neophyl rearrangement was developed, providing 1,2-diphenyl-3-alkyl propanones in moderate to good yields. Moreover, when cyclopropanecarbaldehyde and aryl carbaldehydes were concerned, acylarylation was involved leading to 1,4-dicarbonyl compounds.
Samarium-promoted michael addition between aroyl chlorides and chalcones
Liu, Yongjun,Li, Yuanying,Qi, Yan,Wan, Jun
experimental part, p. 4188 - 4192 (2011/02/25)
A novel Michael addition type reaction between aroyl chlorides and chalcones was realized in the presence of samarium metal when N,N-dimethylformamide was used as a solvent. A variety of 1,4-diketones were thereby synthesized in moderate to good yields. T
Influence of Wavelength on the Photochemistry of Triarylbenzofurodioxin Derivatives
Horspool, William M.,Khalaf, Abedawn I.
, p. 1147 - 1152 (2007/10/02)
The u.v. irradiation of a number of triarylfurobenzodioxins has been carried out at both λ >280 nm and at 254 nm.The outcome of the reaction is to some extent dependent both on the substitution pattern on the bridgehead (9a) aryl group and on the waveleng
