37985-13-0Relevant articles and documents
Phosphorus-recycling wittig reaction: Design and facile synthesis of a fluorous phosphine and its reusable process in the wittig reaction
Yamamoto, Yuki,Kawaguchi, Shin-Ichi,Nishimura, Misaki,Sato, Yuki,Shimada, Yoshihisa,Tabuchi, Akihiro,Nomoto, Akihiro,Ogawa, Akiya
, p. 14684 - 14696 (2020/11/30)
This study shows that phosphorus sources can be recycled using the appropriate fluorous phosphine in the Wittig reaction. The designed fluorous phosphine, which has an ethylene spacer between its phosphorus atom and the perfluoroalkyl group, was synthesized from air-stable phosphine reagents. The synthesized phosphine can be used for the Wittig reaction process to obtain various alkenes in adequate yields and stereoselectivity. The concomitantly formed fluorous phosphine oxide was extracted from the reaction mixture using a fluorous biphasic system. The fluorous phosphine was regenerated by reducing the fluorous phosphine oxide with diisobutylaluminum hydride. Finally, a series of gram scale phosphorus recycling processes were performed, which included the Wittig reaction, separation, reduction, and reuse.
Iron(III)/O2-Mediated Regioselective Oxidative Cleavage of 1-Arylbutadienes to Cinnamaldehydes
Bhowmik, Amit,Fernandes, Rodney A.
supporting information, p. 9203 - 9207 (2019/11/14)
A simple, efficient, and environmentally benevolent regioselective oxidative cleavage of 1-arylbutadienes to cinnamaldehydes mediated by iron(III) sulfate/O2 has been developed. The reaction offered good yields and excellent regioselectivity and showed good functional group tolerance (31 examples). The method is important, as few reports with limited substrate scope are available for such excellent oxidative cleavage of conjugated dienes.
TRIARYLAMINE DERIVATIVE, ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER, AND METHOD FOR PRODUCING ELECTROPHOTOGRAPHIC PHOTOSENSITIVE MEMBER
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Paragraph 0168; 0169; 0170, (2017/05/28)
A triarylamine derivative represented by general formula (1) below. In the general formula (1), R1, R2, R4, R5, R6, R7, R8, and R9 each represent, independently from one another, a hydrogen atom, an optionally substitute alkyl group having a carbon number of at least 1 and no greater than 6, an optionally substituted alkoxy group having a carbon number of at least 1 and no greater than 6, or an optionally substituted aryl group having a carbon number of at least 6 and no greater than 14, R3 represents an alkyl group having a carbon number of at least 1 and no greater than 4, X represents an alkylene group having a carbon number of at least 1 and no greater than 6 or an oxygen atom, and n represents an integer of 1 to 3.
Synthesis of stilbene derivatives via visible-light-induced cross-coupling of aryl diazonium salts with nitroalkenes using-NO2 as a leaving group
Zhang, Na,Quan, Zheng-Jun,Zhang, Zhang,Da, Yu-Xia,Wang, Xi-Cun
supporting information, p. 14234 - 14237 (2016/12/14)
The straightforward visible-light-induced synthesis of stilbene compounds via the cross-coupling of nitroalkenes and diazonium tetrafluoroborates under transition-metal-free conditions is described. The protocol uses green LEDs as light sources and eosin Y as an organophotoredox catalyst. Broad substrate scope and exclusive selectivity for the (E)-configuration of stilbenes are observed. This protocol proceeds via a radical pathway, with nitroalkenes serving as the radical acceptor, and the nitro group is cleaved during the process.
Aryltriolborates as air- and water-stable bases for wittig olefination
Huang, Wenhua,Zhao, Shuang-Hong,Xu, Ning
, p. 359 - 366 (2015/02/19)
Tetrabutylammonium aryltriolborates have been synthesized in 37-66% yield by a one-pot procedure from arylboronic acids, 1,1,1-tris(hydroxymethyl)ethane, and aqueous tetrabutylammonium hydroxide. The aryltriolborates can be used as bases in Wittig reactions of aromatic aldehydes with all three types of phosphorus ylides: stabilized and semistabilized ylides can be generated at room temperature, and nonstabilized ylides at 120 °C (bath temperature).
Syntheses of p-terphenyls and 11,12-dihydroindeno[2,1-a]fluorene by one-pot benzannulation of Diels-Alder reactions of trans-1,2-dichloroethene and dienes
Ho, Jinn-Hsuan,Lin, Yu-Chen,Chou, Li-Ting,Chen, Ying-Zhe,Liu, Wei-Qi,Chuang, Chao-Li
, p. 1991 - 1993 (2013/04/10)
A series of substituted p-terphenyls and 11,12-dihydroindeno[2,1-a]fluorene were successfully synthesized by one-pot benzannulation of Diels-Alder reaction with 1,2-dichloroethene as an acetylene equivalent dienophile. Two chlorine atoms could be good leaving groups to easily undergo subsequent elimination reactions of Diels-Alder products at a high temperature.
Synthesis of 1,4-diarylbuta-1,3-dienes through palladium-catalyzed decarboxylative coupling of unsaturated carboxylic acids
Yamashita, Mana,Hirano, Koji,Satoh, Tetsuya,Miura, Masahiro
experimental part, p. 631 - 636 (2011/04/26)
It has been found that readily available hydroxylated cinnamic acids such as ferulic acid undergo palladium-catalyzed decarboxylative coupling with aryl iodides and internal alkynes in a 1:1:1 manner to produce 1,4-diarylbuta-1,3- dienes. The butadiene synthesis has also been achieved through the coupling of aryl halides with dienoic acids. Some of the products exhibit solid-state fluorescence.
A highly tunable stereoselective olefination of semistabilized triphenylphosphonium ylides with N -Sulfonyl imines
Dong, De-Jun,Li, Hai-Hua,Tian, Shi-Kai
supporting information; experimental part, p. 5018 - 5020 (2010/06/13)
The Wittig reaction involving direct olefination of triphenylphosphonium ylides (Ph3PCHR) with aldehydes is arguably the most often used method for alkene synthesis, but in general it yields mixtures of Z- and E-alkenes for semistabilized triphenylphosphonium ylides (R = aryl or vinyl). We have developed a simple and efficient protocol to improve the stereoselectivity significantly by replacing the aldehydes used in the Wittig reaction with N-sulfonyl imines, which possess distinct electronic and steric properties relative to aldehydes. A broad range of aromatic, α,β-unsaturated, and aliphatic imines bearing appropriate N-sulfonyl groups smoothly undergo olefination reaction with various benzylidenetriphenylphosphoranes or allylidenetriphenylphosphoranes under mild reaction conditions to afford an array of both Z- and E-isomers of conjugated alkenes in good to excellent yields and with greater than 99:1 stereoselectivity. Moreover, this tunable protocol has been successfully applied to the highly stereoselective synthesis of two anticancer agents, DMU-212 and its Z-isomer.
Diphenylamine derivative, production method therefor and electrophotographic photoconductor
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Page/Page column 23-24, (2010/11/29)
The present invention provides a diphenyl amine derivative having the excellent solubility to a solvent and compatibility to a binding resin, an efficient production method therefor, and an electrophotographic photoconductor having the excellent sensitivity, capable of effectively preventing generation of the black dots. A diphenyl amine derivative represented by the following general formula (1) is used: (In the general formula (1), R1 to R12 each are a hydrogen atom, an alkyl group which may have a substituent, or the like, Z is a ring structure linked with a benzene ring, which is a 4 to 8-membered ring including a hydrogen atom, a nitrogen atom, an oxygen atom, a carbon atom or a sulfur atom, m1, m2, n1, n2 each are 0 or 1, m1 + n1 is 1 or 2, and m2 + n2 is 1 or 2.)
Palladium-catalyzed stereoselective synthesis of (E)-stilbenes via organozinc reagents and carbonyl compounds
Wang, Jin-Xian,Wang, Kehu,Zhao, Lianbiao,Li, Hongxia,Fu, Ying,Hu, Yulai
, p. 1262 - 1270 (2007/10/03)
In the presence of a catalytic amount of PdCl2(PPh 3)2 and a silylating agent, organozinc halides reacted with carbonyl compounds to give the corresponding (E)-stilbenes in good to excellent yields under mild conditions. The reaction mechanism is briefly discussed.
