74670-68-1Relevant articles and documents
Decarboxylative julia-kocienski gem-difluoro-olefination of 2-pyridinyl sulfonyldifluoroacetate
Wang, Xiao-Ping,Lin, Jin-Hong,Xiao, Ji-Chang,Zheng, Xing
, p. 928 - 932 (2014)
The decarboxylation of potassium 2-pyridinyl sulfonyldifluoroacetate and its subsequent reaction with aldehydes was found to be an efficient approach for the Julia-Kocienski reaction under mild conditions to give gem-difluoro olefins in moderate to excell
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.