698378-91-5Relevant academic research and scientific papers
Copper-Catalyzed C?H Difluoroalkylation of Coumarins with Fluoroalkyl Bromides
Rao, Min,Wei, Zhenwei,Yuan, Yaofeng,Cheng, Jiajia
, p. 5256 - 5260 (2020/09/11)
An efficient method for the copper-catalyzed selective C?H difluoroalkylation of coumarins and with low cost and readily available ethyl bromodifluoroacetate and N-phenyl bromodifluoroacetamide has been reported. This reaction exhibits good functional group tolerance with respect to coumarins and difluoroalkylation reagents, and several redox-sensitive substrates have been successfully C?H difluoroalkylated in good to high yield. This design could further expand the scope to other heteroarenes, including furan, benzofuran, pyrrole, pyridinone, chromenone, indole, and quinolinone. A mechanism involving copper-catalyzed in-situ generation of fluoroalkyl radical is proposed.
Copper-catalyzed direct C-2 difluoromethylation of furans and benzofurans: Access to C-2 CF2H derivatives
Belhomme, Marie-Charlotte,Poisson, Thomas,Pannecoucke, Xavier
, p. 7205 - 7211 (2014/08/18)
We report herein the first copper-catalyzed C-2 difluoromethylation of furans and benzofurans. The developed methodology allows the selective introduction of the CF2CO2Et moiety at C-2 using CuI as a catalyst. This process was applie
Direct introduction of ethoxycarbonyldifluoromethyl-group to heteroarenes with ethyl bromodifluoroacetate via visible-light photocatalysis
Lin, Qingyu,Chu, Lingling,Qing, Feng-Ling
, p. 885 - 891 (2013/08/23)
A mild and versatile approach for the direct introduction of ethoxycarbonyldifluoromethyl-group to heteroarenes via visible-light photocatalysis has been developed. The new photoredox protocol has enabled the difluoromethylenation of heteroarenes containing a wide range of common functional groups under mild conditions. Copyright
Photochemical substitution of olefins and aromatic compounds with difluoromethyl radicals bearing ester and phosphonate groups
Murakami, Satoru,Ishii, Hideki,Tajima, Toshiki,Fuchigami, Toshio
, p. 3761 - 3769 (2007/10/03)
Efficient and selective substitution of cyclic and acyclic vinyl ethers with photo-generated difluoromethyl radicals bearing ester and phosphonate groups, in the presence of 2,4,6-trimethylpyridine and diphenyl diselenide was successfully carried out to provide the corresponding regioselective unsaturated difluoromethylene adducts selectively. The reaction involves phenylselenyl transfer at an early stage followed by elimination of phenylselenol from the adducts once formed to provide the unsaturated difluoromethylene adducts selectively. This novel photochemical method was successfully extended to aromatic and heteroaromatic substitutions to provide the corresponding α-aryl-α,α-difluoroacetates and α-aryl-α,α- difluoromethylphosphonates in good to moderate yields.
Aromatic substitution with photochemically generated difluoromethyl radicals bearing electron-withdrawing group
Murakami, Satoru,Kim, Shokaku,Ishii, Hideki,Fuchigami, Toshio
, p. 815 - 818 (2007/10/03)
Novel and facile aromatic and heteroaromatic substitutions with difluoromethyl radicals bearing electron-withdrawing group generated by the photo-initiated Se-CF2 bond cleavage of ethyl α,α- difluoro-α-(phenylseleno)acetate and diethyl α,α- difluoromethyl-α-(phenylseleno)phosphonate were successfully carried out to provide the corresponding α-aryl-α,α-difluoroacetates and a-aryl-α,α-difluoromethylphosphonates in good to moderate yields.
