Category: alcohols-buliding-blocksIn 2020 ,《Ring-Opening Lithiation-Borylation of 2-Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters》 was published in Angewandte Chemie, International Edition. The article was written by Nandakumar, Meganathan; Rubial, Belen; Noble, Adam; Myers, Eddie L.; Aggarwal, Varinder K.. The article contains the following contents:
Stereogenic trifluoromethyl-substituted carbon centers are highly sought-after moieties in pharmaceutical and agrochem. discovery. Here, we show that lithiation-borylation reactions of 2-trifluoromethyl oxirane give densely functionalized and highly versatile trifluoromethyl-substituted α-tertiary boronic esters. The intermediate boronate complexes undergo the desired 1,2-rearrangement of the carbon-based group with complete retentive stereospecificity, a process that was only observed in non-polar solvents in the presence of TESOTf. Although the trifluoromethyl group adversely affects subsequent transformations of the α-boryl group, Zweifel olefinations provide trifluoromethyl-bearing quaternary stereocenters substituted with alkenes, alkynes and ketones. In the experiment, the researchers used many compounds, for example, 4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6Category: alcohols-buliding-blocks)
4,4,5,5-Tetramethyl-2-phenyl-1,3,2-dioxaborolane(cas: 24388-23-6) also known as boronate ester, is generally used in metal-catalyzed C-C bond formation reactions like Suzuki–Miyaura reaction.Category: alcohols-buliding-blocks
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts