904928-69-4Relevant academic research and scientific papers
Synthesis of Tetrasubstituted Furans through One-Pot Formal [3 + 2] Cycloaddition Utilizing [1,2]-Phospha-Brook Rearrangement
Aita, Kohei,Ishikawa, Sho,Kondoh, Azusa,Terada, Masahiro
, (2020/03/13)
An efficient method for the synthesis of tetrasubstituted furans was developed by utilizing the [1,2]-phospha-Brook rearrangement under Br?nsted base catalysis. The two-step one-pot formal [3 + 2] cycloaddition involves the nucleophilic addition of a propargyl anion, which is catalytically generated through the [1,2]-phospha-Brook rearrangement, to an aldehyde and the subsequent intramolecular cyclization mediated by N-iodosuccinimide to provide 2,4,5-trisubstituted-3-iodofurans. The present method with readily available substrates provides new access to a wide range of well-organized tetrasubstituted furans.
Leveraging the micellar effect: Gold-catalyzed dehydrative cyclizations in water at room temperature
Minkler, Stefan R. K.,Isley, Nicholas A.,Lippincott, Daniel J.,Krause, Norbert,Lipshutz, Bruce H.
supporting information, p. 724 - 726 (2014/03/21)
The first examples of gold-catalyzed cyclizations of diols and triols to the corresponding hetero- or spirocycles in an aqueous medium are presented. These reactions take place within nanomicelles, where the hydrophobic effect is operating, thereby driving the dehydrations, notwithstanding the surrounding water. By the addition of simple salts such as sodium chloride, reaction times and catalyst loadings can be significantly decreased.
Selective oxygenation of alkynes: A direct approach to diketones and vinyl acetate
Xia, Xiao-Feng,Gu, Zhen,Liu, Wentao,Wang, Ningning,Wang, Haijun,Xia, Yongmei,Gao, Haiyan,Liu, Xiang
supporting information, p. 9909 - 9913 (2015/01/09)
Arylalkynes can be converted into α-diketones with the use of a copper catalyst, and also be transformed into vinyl acetates under metal-free conditions, both in the presence of PhI(OAc)2 as an oxidant at room temperature. A series of substituted α-diketones were prepared in moderate to good yields. A variety of vinyl halides could be regio- and stereo-selectively synthesized under mild conditions, and I, Br and Cl could be all easily embedded into the alkynes. This journal is
A convenient synthesis of tetrasubstituted furans from propargylic dithioacetals
Tseng, Jui-Chang,Chen, Jia-Hong,Luh, Tien-Yau
, p. 1209 - 1212 (2007/10/03)
A convenient procedure for the regioselective synthesis of tetrasubstituted furans from the corresponding propargylic dithioacetals is described. Treatment of propargylic dithioacetals with n-BuLi and an aldehyde followed by mercuric acetate promoted annu
