5621-69-2Relevant articles and documents
Photoenolization/nucleophilic addition enables direct access to 3-alkyl-3-hydroxy-indolin-2-ones
Wang, Zhi-Lv,Tang, Li,Zeng, Wei-Mei,He, Yan-Hong,Guan, Zhi
, (2022/03/27)
A light-driven, catalyst- and additive-free photoenolization/nucleophilic addition reaction for the synthesis of 3-benzyl-3-hydroxyindolin-2-ones is presented. In this reaction, 2-methylbenzophenones undergo light-induced enolization process to afford hydroxy-o-quinodimethanes (hydroxy-o-QDMs), which are then immediately captured by the electrophilic isatins. The reaction utilizes green and clean light energy to realize the C–H activation of the inert benzyl position of 2-methylbenzophenones. This method tolerates a wide scope of substrates and provides concise access to a series of novel 3-benzyl-3-hydroxyindolin-2-ones with 60–99% yields.
Palladium-phosphinous acid-catalyzed cross-coupling of aryl and acyl halides with aryl-, alkyl-, and vinylzinc reagents
Xu, Hanhui,Ekoue-Kovi, Kekeli,Wolf, Christian
, p. 7638 - 7650 (2008/12/22)
(Chemical Equation Presented) Several palladium-phosphinous acids have been prepared and employed in cross-coupling reactions of aryl or acyl halides with aliphatic and aromatic organozinc reagents. The POPd7-catalyzed reaction of aryl halides, including electron-rich aryl chlorides, and arylzinc reagents was found to afford biaryls exhibiting alkoxy, alkylthio, amino, ketone, cyano, nitro, ester, and heteroaryl groups in 75-93% yield. Excellent results were obtained with sterically hindered substrates which gave di- and tri-ortho-substituted biaryls in up to 92% yield. Aryl halides also undergo POPd7-catalyzed aryl-vinyl and aryl-alkyl bond formation under mild conditions. Styrenes and alkylarenes were prepared in 79-93% yield from aryl halides and vinyl or alkylzinc reagents. The replacement of aryl halides by acyl halides provides access to ketones which were produced in up to 98% yield when POPd was used as catalyst. This approach overcomes the limited substrate scope, reduced regiocontrol, and low functional group tolerance of traditional Friedel-Crafts acylation methods.