80493-89-6Relevant articles and documents
Suzuki-Miyaura Cross-Coupling of Sulfoxides
Abduhulam, Hayrul,Cao, Changsheng,Chen, Qianwei,Dang, Yanfeng,Li, Chengxi,Shi, Yanhui,Wu, Shufeng,Yan, Shuqin
, p. 8168 - 8176 (2020/09/18)
The utilization of diphenyl sulfoxides as versatile electrophilic coupling partners for the Suzuki-Miyaura reaction via C-S bond cleavage was successfully developed under palladium-N-heterocyclic carbene catalysis. The reactions showed good functional group compatibility, proceeded well under mild conditions, and provided biaryls in yields of up to 96%. A wide range of useful functional groups, such as fluoro, chloro, ether, hydroxyl, amide, cyano, keto, trimethylsilyl (TMS), and ester were tolerated under the reaction conditions; however, the use of phenylboronic anhydride and arylboronic acid pinacol esters generally would lead low yields. Good regioselectivity for the electron-poor phenyl group was achieved when unsymmetrical diphenyl sulfoxides were used. The protocol is applicable at the gram scale even with half the amount of catalyst. Density functional theory calculations were performed to investigate the reaction mechanism, indicating that the reaction occurred through oxidative addition, transmetalation, and reductive elimination to provide the final coupling product.
Synthese und fluessigkristalline Eigenschaften 2,6-disubstituierter Naphtaline
Lauk, Urs H.,Skrabal, Peter,Zollinger, Heinrich
, p. 1406 - 1426 (2007/10/02)
The syntheses and the mesomorphic properties of a series of novel 2,6-disubstituted naphthalenes are described. 4-benzonitriles 5 and 4-benzonitriles 8 exhibit wide-range nematic mesophases. 6,6'-Di(n-Alkyl)-2,2'-binaphthyls 6 have been isolated as by-products from the reaction mixtures of 5.Some of these novel compounds have polymorphic properties.The esters 13 and 15 of 4-(6-hydroxy-2-naphthyl)benzonitrile show enhanced mesophase stabilities which reach maximum values in the series of α,β-unsaturated esters 15.The 4-(n-pentyl)benzoate 14 of the same (hydroxynaphthyl)benzonitrile has a melting point of 125 deg and a clearing point of > 310 deg.This particular derivative belongs to those liquid-crystalline compounds having the broadest purely nematic-phase range.In addition, (RS)-4-(2-pentyl-6-chromanyl)benzonitrile (20) and three compounds with two and four laterally arranged CN groups at the bicyclooctene, bicyclooctadiene, and phenyl-ring systems 31-33 were synthesized.Only 20 shows mesomorphic properties.
