Radical reactivity of α,β,β-trifluoroacrylic ester: Facile approach to γ-silyloxy-α,β,β-trifluorobutyric acid derivatives involving regioselective nucleophilic radical addition reaction

Tamamoto, Ken; Yamada, Shigeyuki; Higashi, Masao; Konno, Tsutomu; Ishihara, Takashi

doi:10.1016/j.jfluchem.2016.08.011

Cited by 5 publications

(1 citation statement)

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“…Benzaldehyde-ketyl radical generated through the reaction of benzaldehyde with (TMS) 3 Si • radical was shown to add efficiently to fluorinated esters such as 256 to afford trifluorobutanoic acid derivatives 257 with satisfying yield but low diastereoselectivity (Scheme 74). 184 The reaction could be extended to several substituted benzaldehydes and arylketones. Alkyl aldehydes did not form the ketyl radical, and the reaction under these conditions led instead to the addition of the (TMS) 3 Si • radical to 256.…”

Section: Intermolecular C−c Bond Formationmentioning

confidence: 99%

Thirty Years of (TMS)₃SiH: A Milestone in Radical-Based Synthetic Chemistry

et al. 2018

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This review is an update on tris(trimethylsilyl)silane, TTMSS, in organic chemistry, focusing on the advancements of the past decade. The overview includes a wide range of chemical processes and synthetic strategies under different experimental conditions, including functional group insertion and transformations, as well as preparation of complex molecules, natural products, polymers, surfaces, and new materials. These results reveal how TTMSS has matured over the past 30 years, and they further establish its value as a free radical reagent with widespread academic and industrial applications.

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Section: Intermolecular C−c Bond Formationmentioning

confidence: 99%