1459-20-7Relevant articles and documents
An unexpected formation of benzoyl benzoin from benzil during the attempted Knoevenagel type condensation with dimethylmalonate (or malononitrile)
Shyam Sundar,Bedekar, Ashutosh V.
, p. 2745 - 2747 (2012)
An unexpected product, 2-oxo-1,2-diphenylethyl benzoate (benzoyl benzoin), was isolated during the attempted Knoevenagel reaction of benzil and dimethylmalonate (or malononitrile) in the presence of potassium carbonate. The product was confirmed by spectral analysis as well as by single crystal studies and a mechanism is proposed to explain its formation.
Ionization and Anion-π+ Interaction: A New Strategy for Structural Design of Aggregation-Induced Emission Luminogens
Wang, Jianguo,Gu, Xinggui,Zhang, Pengfei,Huang, Xiaobo,Zheng, Xiaoyan,Chen, Ming,Feng, Haitao,Kwok, Ryan T. K.,Lam, Jacky W. Y.,Tang, Ben Zhong
, p. 16974 - 16979 (2017)
Recent years have witnessed the significant role of anion-π+ interactions in many areas, which potentially brings the opportunity for the development of aggregation-induced emission (AIE) systems. Here, a new strategy that utilized anion-π
Desyl and phenacyl as versatile, photocatalytically cleavable protecting groups: A classic approach in a different (visible) light
Speckmeier, Elisabeth,Zeitler, Kirsten
, p. 6821 - 6826 (2017/11/06)
A highly efficient, catalytic strategy for the deprotection of classical phenacyl (Pac) as well as desyl (Dsy) protection groups has been developed using visible light photoredox catalysis. The deliberate use of a neutral two-phase acetonitrile/water mixture with K3PO4 applying catalytic amounts of [Ru(bpy)3](PF6)2 in combination with ascorbic acid is the key to this truly catalytic deprotection of Pac- and Dsy-protected carboxylic acids. Our mild yet robust protocol allows for fast and selective liberation of the free carboxylic acids in very good to quantitative yields, while only low catalyst loadings (1 mol %) are required. Both Pac and Dsy, easily introduced from commercially available precursors, can be applied for the direct protection of carboxylic acids and amino acids, offering orthogonality to a great variety of other common protecting groups. We further demonstrate the general applicability and versatility of these formerly underrated protecting groups in combination with our catalytic cleavage conditions, as underscored by the gained high functional group tolerance. Moreover, this method could successfully be adapted to the requirements of solidphase synthesis. As a proof of principle for an efficient visible light, photocatalytic linker cleavage, a Boc-protected tripeptide was split off from commercially available brominated Wang resin.
Palladium-Catalyzed Chemo- and Enantioselective C?O Bond Cleavage of α-Acyloxy Ketones by Hydrogenolysis
Chen, Jianzhong,Zhang, Zhenfeng,Liu, Delong,Zhang, Wanbin
, p. 8444 - 8447 (2016/07/19)
A chemoselective C?O bond cleavage of the ester alkyl side-chain of α-acyloxy ketones was realized for the first time by a highly efficient palladium-catalyzed hydrogenolysis (S/C=6000, the highest catalytic efficiency by far). Furthermore, a kinetic resolution of α-acyloxy ketones was first developed by enantioselective hydrogenolysis with good yields and up to 99 % ee.