84750-92-5Relevant articles and documents
-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.
Pd-Catalyzed Selective Carbonylation of gem-Difluoroalkenes: A Practical Synthesis of Difluoromethylated Esters
Liu, Jiawang,Yang, Ji,Ferretti, Francesco,Jackstell, Ralf,Beller, Matthias
supporting information, p. 4690 - 4694 (2019/03/13)
The first catalyst for the alkoxycarbonylation of gem-difluoroalkenes is described. This novel catalytic transformation proceeds in the presence of Pd(acac)2/1,2-bis((di-tert-butylphosphan-yl)methyl)benzene (btbpx) (L4) and allows for an efficient and straightforward access to a range of difluoromethylated esters in high yields and regioselectivities. The synthetic utility of the protocol is showcased in the practical synthesis of a Cyclandelate analogue using this methodology as the key step.
A versatile difluorovinylation method: Cross-coupling reactions of the 2,2-difluorovinylzinc-TMEDA complex with alkenyl, alkynyl, allyl, and benzyl halides Dedicated to Professor Iwao Ojima on the occasion of his 70th birthday.
Ichitsuka, Tomohiro,Takanohashi, Tsuyoshi,Fujita, Takeshi,Ichikawa, Junji
, p. 29 - 37 (2015/03/04)
A thermally stable 2,2-difluorovinylzinc-TMEDA complex was prepared via a deprotonation-transmetallation sequence starting from commercially available 1,1-difluoroethylene. The complex thus formed was successfully applied to transition metal-catalyzed cross-coupling reactions with a wide range of organic halides, which led to the syntheses of 2,2-difluorovinyl compounds. On treatment with the difluorovinylzinc-TMEDA complex in the presence of an appropriate palladium or copper catalyst, alkenyl, alkynyl, allyl, and benzyl halides effectively underwent difluorovinylation to afford 1,1-difluoro-1,3-dienes, 1,1-difluoro-1,3-enynes, 1,1-difluoro-1,4-dienes, and (3,3-difluoroallyl)arenes, respectively.