55577-65-6Relevant academic research and scientific papers
An efficient synthesis of benzothiazole using tetrabromomethane as a halogen bond donor catalyst
Kazi, Imran,Sekar, Govindasamy
, p. 9743 - 9756 (2019/12/02)
An efficient and mild protocol has been developed for the synthesis of 2-substituted benzothiazole under solvent- and metal-free conditions using CBr4 as the catalyst. This process involves the activation of a thioamide through halogen bond formation between the sulphur atom of the thioamide and bromine atom of the CBr4 molecule. The presence of halogen-bonding interaction between N-methylthioamides and tetrabromomethane has been demonstrated with several control experiments, spectroscopic analysis and density functional theory (DFT). This methodology has a wide substrate scope for the synthesis of both 2-alkyl and 2-aryl substituted benzothiazoles.
Intramolecular 1,5-H transfer reaction of aryl iodides through visible-light photoredox catalysis: A concise method for the synthesis of natural product scaffolds
Chen, Jian-Qiang,Wei, Yun-Long,Xu, Guo-Qiang,Liang, Yong-Min,Xu, Peng-Fei
supporting information, p. 6455 - 6458 (2016/05/24)
The intramolecular 1,5-H transfer reaction of the aryl radicals generated from unactivated aryl iodides by photocatalysis is described. The features of this transformation are operational simplicity, excellent yields, mild reaction conditions, and good fu
Generation of Hydrogen from Water: A Pd-Catalyzed Reduction of Water Using Diboron Reagent at Ambient Conditions
Ojha, Devi Prasan,Gadde, Karthik,Prabhu, Kandikere Ramaiah
supporting information, p. 5062 - 5065 (2016/10/14)
Production of hydrogen from renewable sources, particularly from water, is an intensive area of research, which has far-reaching relevance in hydrogen economy. A homogeneous catalytic method is presented for producing clean hydrogen gas from water, in a reaction of water with a diboron compound as the reductant, under ambient reaction conditions. The Pd-catalytic system is stable in water and displays excellent recyclability. Hydroxy analogues such as alcohols are compatible with the Pd/B2Pin2 system and generate hydrogen gas efficiently. The B2Pin2-H2O system, in the presence of palladium, is an excellent catalytic system for selective hydrogenation of olefins.
Transition metal and base-free synthesis of 3,3-diaryl-2-oxindoles from 2,2,N-triarylacetamides
Lim, Jin Woo,Kim, Ko Hoon,Moon, Hye Ran,Kim, Jae Nyoung
supporting information, p. 784 - 787 (2016/02/03)
A transition metal and base-free synthesis of 3,3-diaryl-2-oxindoles has been developed from 2,2,N-triarylacetamides in the presence of montmorillonite K-10 in 1,2-dichlorobenzene under O2 balloon atmosphere.
Nickel-catalyzed dehydrogenative cross-coupling: Direct transformation of aldehydes into esters and amides
Whittaker, Aaron M.,Dong, Vy M.
supporting information, p. 1312 - 1315 (2015/01/30)
By exploring a new mode of nickel-catalyzed cross-coupling, a method to directly transform both aromatic and aliphatic aldehydes into either esters or amides has been developed. The success of this oxidative coupling depends on the appropriate choice of catalyst and organic oxidant, including the use of either α,α,α-trifluoroacetophenone or excess aldehyde. Mechanistic data that supports a catalytic cycle involving oxidative addition into the aldehyde C-H bond is also presented.
Amide bond formation through iron-catalyzed oxidative amidation of tertiary amines with anhydrides
Li, Yuanming,Ma, Lina,Jia, Fan,Li, Zhiping
, p. 5638 - 5646 (2013/07/26)
A general and efficient method for amide bond synthesis has been developed. The method allows for synthesis of tertiary amides from readily available tertiary amines and anhydrides in the presence of FeCl2 as catalyst and tert-butyl hydroperoxide in water (T-Hydro) as oxidant. Mechanistic studies indicated that the in situ-generated α-amino peroxide of tertiary amine and iminium ion act as key intermediates in this oxidative transformation.
Synthesis of indolones via radical cyclization of N-(2-halogenoalkanoyl)- substituted anilines
Nishio, Takehiko,Iseki, Kyoko,Araki, Norihito,Miyazaki, Takenori
, p. 35 - 41 (2007/10/03)
The radical reactions of N-(2-halogenoalkanoyl)-substituted anilines (anilides) of type 1 have been investigated under various conditions. Treatment of compounds 1a-1o with Bu3SnH in the presence of (2,2′-azobis(isobutyronitrile) (AIBN) afforded a mixture of the indolones (oxindoles) 2a-2o and the reduction products 5a-5o (Table 1). In contrast, the N-unsubstituted anilides 1p-1s, 1u, and 1v gave the corresponding reduction products exclusively (Table 1). Similar results were obtained by treatment of 1 with Ni powder (Table 2) or wth Et3B (Table 3). Anilides with longer N-(phenylalkyl) chains such as 6 and 7 were inert towards radical cyclization, with the exception of N-benzyl-2-bromo-N,2-dimethylpropanamide (6b), which, upon treatment with Ni powder in i-PrOH, afforded the cyclized product 9b in low yield (Table 4). Upon irradiation, the extended anilides 6, 7, 10, and 11 yielded the corresponding dehydrobromination products exclusively (Table 5).
The extraordinary reactions of phenyldimethylsilyllithium with N,N-disubstituted amides
Buswell, Marina,Fleming, Ian,Ghosh, Usha,Mack, Stephen,Russell, Matthew,Clark, Barry P.
, p. 3006 - 3017 (2007/10/03)
The reactions of the silyllithium reagent with tertiary amides was discussed. The enediamines were easily isomerized from cis to trans, easily oxidized to dienediamines and were hydrolyzed to α-aminoketones. If the two equivalents of the silyllithium reagent were used, the product was an α-silylamine. The results show that each member of the homologous series of amides gives rise to a substantially different product.
Diethylphosphine oxide (DEPO): High-yielding and facile preparation of indolones in water
Khan, Tanweer A.,Tripoli, Regis,Crawford, James J.,Martin, Concepcion G.,Murphy, John A.
, p. 2971 - 2974 (2007/10/03)
(Matrix presented) Indolones are prepared in excellent yield at 80°C in water by radical reaction (aryl radical formation, hydrogen atom abstraction, cyclization, and rearomatization) mediated by the reagent diethylphosphine oxide (DEPO). The reaction fea
A general and practical method of synthesis of 2-disubstituted-1- chloro- and 1-bromoenamines
Ghosez, Leon,George-Koch, Isabelle,Patiny, Luc,Houtekie, Marc,Bovy, Philippe,Nshimyumukiza, Prosper,Phan, Thao
, p. 9207 - 9222 (2007/10/03)
Disubstituted-α-chloroenamines are useful synthetic intermediates which had earlier been prepared by the reaction of tertiary amides with phosgene. The toxicity of the latter led us to systematically investigate new synthetic routes towards α-chloro- and
