5825-19-4Relevant academic research and scientific papers
A new insight into the push-pull effect of substituents via the stilbene-like model compounds
Cao, Chaotun,Cao, Chenzhong,Zeng, Zhao
, (2022/02/01)
In this paper, authors report on 1-pyridyl-2-arylethenes, 1-furyl-2-arylethylenes, 1,2-diphenylpropylenes and substituted cinnamyl anilines as stilbene-like model compounds to investigate the factors dominating the push-pull effect of substituents via usi
Determination and application of the excited-state substituent constants of pyridyl and substituted phenyl groups
Cao, Chao-Tun,Yan, Lu,Cao, Chenzhong
supporting information, (2021/05/21)
Thirty six 1-pyridyl-2-arylethenes XCH=CHArY (abbreviated XAEY) were synthesized, in which, X is 2-pyridyl, 3-pyridyl and 4-pyridyl and Y is OMe, Me, H, Br, Cl, F, CF3, and CN. Their ultraviolet absorption spectra were measured in anhydrous ethanol, and their wavelengths of absorption maximum λmax were recorded. Also, the 234 λmax values of 1-substituted phenyl-2-arylethylene compounds (XAEY, where X is substituted phenyl) were collected. The excited-state substituent constants (Formula presented.) of three pyridyl groups and 23 substituted phenyl groups (total of 26) were obtained by means of curve-fitting method. Taking the λmax values of 358 samples of bi-arylethene derivatives as a data set and 126 samples of bi-aryl Schiff bases (including nine compounds synthesized by this work) as another data set, quantitative correlation analyses were performed by employing the obtained (Formula presented.) as a parameter, and good results were obtained for the two data sets. The reliability of the obtained (Formula presented.) values was verified. The results of this paper can provide excited-state substituent constants for the study and application of optical properties of conjugated organic compounds containing aryl groups.
Mizoroki-Heck reactions catalyzed by palladium dichloro-bis(aminophosphine) complexes under mild reaction conditions. the importance of ligand composition on the catalytic activity
Oberholzer, Miriam,Frech, Christian M.
supporting information, p. 1678 - 1686 (2013/10/01)
Dichloro-bis(aminophosphine) complexes of palladium with the general formula [(P{(NC5H10)3-n(C6H 11)n})2Pd(Cl)2] (where n = 0-2) are easily accessible, cheap and air stable, highly active and universally applicable C-C cross-coupling catalysts, which exhibit an excellent functional group tolerance. The ligand composition of amine-substituted phosphines (controlled by the number of P-N bonds) was found to effectively determine their catalytic activity in the Heck reaction, for which nanoparticles were demonstrated to be their catalytically active form. While dichloro{bis[1, 1′,1′′-(phosphinetriyl)tripiperidine]}palladium (1), the least stable complex (towards protons) within the series of [(P{(NC5H 10)3-n(C6H11)n}) 2Pd(Cl)2] (where n = 0-3), is a highly active Heck catalyst at 100 °C and, hence, a rare example of an effective and versatile Heck catalyst that efficiently operates under mild reaction conditions (100 °C or below), a significant successive drop in activity was noticed for dichloro-bis(1,1′-(cyclohexylphosphinediyl)dipiperidine)palladium (2, with n = 1), dichloro-bis(1-(dicyclohexylphosphinyl)piperidine)palladium (3, with n = 2) and dichloro-bis(tricyclohexylphosphine)palladium (4, with n = 3), of which the latter is essentially inactive (at least under the reaction conditions applied). This trend was explained by the successively increasing complex stability and its ensuing retarding effect on the (water-induced) generation of palladium nanoparticles thereof. This interpretation was experimentally confirmed (initial reductions of 1-4 into palladium(0) complexes of the type [Pd(P{(NC5H10)3-n(C6H 11)n})2] (where n = 0-3) were excluded to be the reason for the activity difference observed as well as molecular (Pd 0/PdII) mechanisms were excluded to be operative) and thus demonstrates that the catalytic activity of dichloro-bis(aminophosphine) complexes of palladium can-in reactions where nanoparticles are involved-effectively be controlled by the number of P-N bonds in the ligand system.
Ligand-free palladium-catalysed oxidative Heck reaction of 4-vinylpyridine with arylboronic acids: Selective synthesis of (E)-4-styrylpyridines
Shi, Chuanli,Ding, Jinchang,Jiang, Jun,Chen, Jiuxi,Wu, Huayue,Liu, Miaochang
supporting information; experimental part, p. 322 - 325 (2012/09/21)
A ligand-free palladium-catalysed oxidative Heck reaction of various arylboronic acids with 4-vinylpyridine has been developed, achieving (E)-4-styrylpyridines with high selectively in moderate to good yields. A plausible mechanism for the formation of (E)-4-styrylpyridines has been proposed.
Regiospecific [2 + 2] photocyclodimerization of trans-4-styrylpyridines templated by cucurbit[8]uril
Nakamura, Asao,Irie, Hiromi,Hara, Shuhei,Sugawara, Mai,Yamada, Shinji
scheme or table, p. 1496 - 1500 (2012/06/01)
Addition of HCl accelerated the photocyclodimerization of trans-4-styrylpyridine 1a in methanol and increased the yield of syn-head-to-tail (syn-HT) dimer 2a through the effect of cation-π interactions between the pyridinium ion of one molecule and the phenyl group of the other. We examined the photoirradiation products of derivatives of 1a having alkyl substituents on the phenyl group (1b-1f). The effect of the alkyl substituent on product distribution was rather limited for the photoreaction in MeOH solutions. However, the substituents had a distinct effect on the product distribution for the photoreaction of the inclusion complexes of hydrochloride salts of trans-4-styrylpyridines with cucurbit[8]uril in aqueous solutions. Introducing an alkyl group at the 2- or 3-position of the phenyl group completely shifted the major product from the syn-HT dimer to the syn-head-to-head (syn-HH) dimer. By adjusting the balance of host-guest interactions and cation-π interactions between guest molecules through systematic changes in the substituents on the phenyl ring of trans-4-styrylpyridine, we could change the orientation of the reactant molecules in the host cavity, resulting in a change of the major regioisomer of the photocyclodimerization products. The Royal Society of Chemistry and Owner Societies.
Practical Heck-Mizoroki coupling protocol for challenging substrates mediated by an N-heterocyclic carbene-ligated palladacycle
Kantchev, Eric Assen B.,Peh, Guang-Rong,Zhang, Chi,Ying, Jackie Y.
supporting information; experimental part, p. 3949 - 3952 (2009/05/30)
(Chemical Equation Presented) A highly active, N-heterocyclic carbene-palladacycle precatalyst for the Heck-Mizoroki reaction was rationally designed. The complex can be synthesized on a large scale in excellent yield by a novel, one-pot, three-component reaction and is tolerant to air, moisture, and long-term storage. A wide range of challenging substrates is successfully coupled under a simple and user-friendly reaction protocol.
