17090-09-4Relevant academic research and scientific papers
Synthesis of 4-Trifluoromethylated 1,3-Butadienes via Palladium Catalyzed Heck Reaction
Li, Yang,Hao, Meng,Chang, Yu-Chen,Liu, Yuan,Wang, Wen-Fei,Sun, Ning,Zhu, Wen-Qing,Gao, Ziwei
supporting information, p. 2962 - 2966 (2021/08/23)
1,3-Butadiene plays a key role in modern synthetic chemistry and biochemistry because it is a key intermediate in the synthesis of many drugs. A new and effective method for the synthesis of 4-trifluoromethylated 1,3-butadiene through the fluorinated Heck reaction catalyzed by Pd(0) is described. Without additives, 1-chloro-3,3,3-trifluoropropene (an inexpensive CF3 structural unit that is harmless to ozone) reacts with enamide to synthesize 4-trifluoromethylated 1,3-butadienes with good yield, high regioselectivity and chemical selectivity, and strong tolerance of substrate functional groups such as alkynes, aldehyde, and ester groups.
Rh-Catalyzed Domino Addition-Enolate Arylation: Generation of 3-Substituted Oxindoles via a Rh(lll) Intermediate
Jang, Young Jin,Yoon, Hyung,Lautens, Mark
supporting information, p. 3895 - 3897 (2015/08/18)
A Rh-catalyzed domino conjugate addition-arylation sequence via a Rh(III) intermediate is reported. This process involving a proposed intramolecular oxidative addition of a rhodium enolate was utilized to achieve the synthesis of 3-substituted oxindole derivatives in moderate to excellent yields.
Systematic study of the glutathione (GSH) reactivity of N-arylacrylamides: 1. Effects of aryl substitution
Cee, Victor J.,Volak, Laurie P.,Chen, Yuping,Bartberger, Michael D.,Tegley, Chris,Arvedson, Tara,McCarter, John,Tasker, Andrew S.,Fotsch, Christopher
, p. 9171 - 9178 (2015/12/23)
Success in the design of targeted covalent inhibitors depends in part on a knowledge of the factors influencing electrophile reactivity. In an effort to further develop an understanding of structure-reactivity relationships among N-arylacrylamides, we determined glutathione (GSH) reaction rates for a family of N-arylacrylamides independently substituted at ortho-, meta-, and para-positions with 11 different groups common to inhibitor design. We find that substituent effects on reaction rates show a linear Hammett correlation for ortho-, meta-, and para-substitution. In addition, we note a correlation between 1H and 13C NMR chemical shifts of the acrylamide with GSH reaction rates, suggesting that NMR chemical shifts may be a convenient surrogate measure of relative acrylamide reactivity. Density functional theory calculations reveal a correlation between computed activation parameters and experimentally determined reaction rates, validating the use of such methodology for the screening of synthetic candidates in a prospective fashion.
Synthesis of [11C]/[13C]acrylamides by palladium-mediated carbonylation
Eriksson, Jonas,Aberg, Ola,Langstroem, Bengt
, p. 455 - 461 (2008/02/03)
Two methods are presented for the synthesis of acrylamides labelled with 11C (β+, t1/2 = 20.4 min) and 13C in the carbonyl position. In the first method, [1- 11C]acrylic acid is synthesised from [11C]carbon monoxide by palladium-mediated hydroxycarbonylation of acetylene. The labelled carboxylic acid is converted into the acyl chloride and subsequently treated with amine to yield N-benzyl[carbonyl-11C]acrylamide. The second method utilizes [11C]carbon monoxide in a palladium-mediated carbonylative cross-coupling of vinyl halides and amines. A higher radiochemical yield is achieved with the latter method and the amount of amine needed is decreased to 1/20. The 11C-labelled acrylamides were isolated in up to 81 % decay-corrected radiochemical yield. Starting from 10 ± 0.5 GBq of [ 11C]carbon monoxide, N-benzyl[carbonyl-11C]acrylamide was obtained in 4 min with a specific radioactivity of 330 ± 4 GBq μmol-1. Co-labelling with 11C and 13C enabled confirmation of the labelled position by 13C NMR spectroscopy. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Synthesis of Oxindole Derivatives from N-Alkenyl-o-Chloroanilides with Zero-Valent Nickel Complex
Canoira, L.,Rodriguez, J. G.
, p. 1511 - 1518 (2007/10/02)
Oxindole derivatives have been obtained from N-alkenyl-o-chloroanilides by reaction with tetrakis(triphenylphoaphine)nickel(0) in toluene as solvent in good yields.A detailed analysis of all the products of the reaction allows to confirm the postulated mechanism of the cyclization reaction.The o-chloroanilides of the 3-cyclohexenylacetic acid fails in the cyclization reaction, since the torsional hindrance seems to avoid that the endocyclic double bond may be orthogonally to the ortho-?-nickel complex intermediate on the aromatic ring.
