84750-93-6Relevant articles and documents
Stereoselective formation of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem?difluoroalkenes with lithium organoborates
Huang, Weichen,Shen, Qilong,Xiao, Yisa
supporting information, (2022/02/02)
A method for stereoselective construction of Z-monofluoroalkenes by nickel-catalyzed defluorinative coupling of gem?difluoroalkenes in mild conditions was described. The combination of lithium organoborate and ZnBr2 generated in situ lithium ar
Fluoride-Triggered Synthesis of 1-Aryl-2,2-difluoroalkenes via Desilylative Defluorination of (1-Aryl)-2,2,2-trifluoroethyl-silanes
Carreras, Virginie,Ollevier, Thierry
, p. 13160 - 13168 (2021/09/18)
An efficient route for the synthesis of 1-aryl-2,2-difluoroalkenes via 1,2-desilylative defluorination is disclosed. Only a catalytic amount of fluoride source is required to initiate the desilylation and afford gem-difluoroalkenes in very good to quantitative yields, using mild reaction conditions in dimethyl carbonate as a green solvent. This reaction uses (1-aryl)-2,2,2-trifluoroethyl-silanes, which are easily prepared via the insertion reaction of trifluoroethyl diazo alkanes into the Si-H bond of tertiary organosilanes. (1-Aryl)-perfluoroalkyl-silanes cleanly afford the corresponding (Z)-1-benzylideneperfluoroalkanes, which upon hydrodefluorination furnish the (E)-β(perfluoroalkyl)styrene derivatives with excellent yield and complete stereoselectivity. A one-pot system involving sequential insertion and desilylative-defluorination is also suitable for this transformation. This method demonstrates the usefulness of organosilanes toward the preparation of fluorinated alkenes as synthetically useful targets.
-Annulation of gem-Difluoroalkenes and Pyridinium Ylides: Access to Functionalized 2-Fluoroindolizines
Zhang, Jun-Qi,Hu, Dandan,Song, Jinyu,Ren, Hongjun
, p. 4646 - 4660 (2021/04/06)
A [3 + 2]-annulation of gem-difluoroalkenes and pyridinium ylides was developed employing ambient air as the sole oxidant in an open-vessel manner, affording a series of multifunctionalized 2-fluoroindolizines in moderate to good yields. In this reaction, gem-difluoroalkene acts as a C2 synthon and entirely avoids the competitive addition-elimination process, which provides facile access to 2-fluoroindolizines.