1286694-32-3Relevant academic research and scientific papers
Highly stereoselective and one-pot synthesis of tetra-substituted monofluoroalkenes with aldehydes and fluorobis(phenylsulfonyl)methane
Shen, Xiao,Ni, Chuanfa,Hu, Jinbo
, p. 878 - 884 (2013/08/23)
A highly stereoselective synthesis of tetrasubstituted monofluoroalkenes with aldehydes and fluorobis(phenylsulfonyl)methane (FBSM) in one pot has been developed. The reaction was amenable to para- and meta-substituted aryl aldehydes, 2-naphthaldehyde, and cinnamaldehyde, giving phenylsulfonyl- substituted monofluoroalkenes in 40%-86% yields with 98/2-99/1 Z/E ratios. The presence of the sulfonyl group enables the further transformation of the products into more useful monofluoroalkenes. Highly stereoselective and one-pot synthesis of tetrasubstituted monofluoroalkenes with fluorobis(phenylsulfonyl) methane (FBSM) as the fluoroolefination reagent has been developed. This protocol is amenable to the transformation of non-enolizable aldehydes with less sterically demanding substituents. For enolizable aldehydes and sterically hindered aromatic aldehydes, the reaction furnishes carbonyl addition products. Copyright
Nucleophilic fluoromethylation of aldehydes with fluorobis(phenylsulfonyl) methane: The importance of strong Li-O coordination and fluorine substitution for C-C bond formation
Shen, Xiao,Zhang, Laijun,Zhao, Yanchuan,Zhu, Lingui,Li, Guangyu,Hu, Jinbo
, p. 2588 - 2592 (2011/04/25)
The tighter, the better! Fluorobis(phenylsulfonyl)methane reacts readily with aldehydes to give addition products in excellent yields (see scheme; LiHMDS=lithium hexamethyldisilazide), which is in sharp contrast to previous findings. Both strong Li-O coordination at low temperature and fluorine substitution play important roles in successful C-C bond formation. Copyright
