化学
催化作用
三氟甲基
镍
键裂
硅氢加成
药物化学
劈理(地质)
有机化学
组合化学
光化学
断裂(地质)
工程类
岩土工程
烷基
作者
Ryohei Doi,Masashi Yasuda,Naoki Kajita,Kenta Koh,Sensuke Ogoshi
摘要
Perfluoroalkyl compounds are persistent environmental pollutants due to their strong C(sp3)-F bonds. Hydrodefluorination has emerged as a potential alternative disposal method for perfluoroalkyl compounds. Although the transformation of trifluoromethyl arenes into the corresponding methyl arenes has been studied by several research groups, hydrodefluorination reactions of longer perfluoroalkyl chains remain rare. Herein, we report exhaustive hydrodefluorination reactions of pentafluoroethyl arenes and longer-chain analogues using molecular nickel catalysis. Despite the cleavage of multiple C(sp3)-F bonds, the reaction already proceeds upon gentle heating (60 °C). A mechanistic investigation indicated that the reaction proceeds via benzylic hydrodefluorination reactions followed by homobenzylic ones. We reveal the multiple roles of the Ni catalyst, which include C-F bond cleavage, promotion of HF elimination, and hydrosilylation.
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