Nucleophilic fluoroalkylation of (bromomethyl)pinacolborane using silicon reagents

A Convergent, Modular Approach to Functionalized 2,1-Borazaronaphthalenes from 2-Aminostyrenes and Potassium Organotrifluoroborates

“…The approach described herein allows the use of diverse, readily available, primary and secondary alkyltrifluoroborates employed in a direct, straightforward, one-step synthesis of 2-alkyl-2,1-borazaronaphthalenes with yields up to 58% (Table 5). For example, β,β,β-trifluoroethyltrifluoroborate 19 was effectively used in the reaction, resulting in the corresponding product in 40% yield (entry 3). An acyclic secondary trifluoroborate was successfully utilized, and the desired product was obtained in 58% yield (entry 4).…”

Ring‐Opening Lithiation–Borylation of 2‐Trifluoromethyl Oxirane: A Route to Versatile Tertiary Trifluoromethyl Boronic Esters

“…Asymmetric versions of this reaction have also been developed using engineered enzymes . Dilman showed that trifluoromethyl boronate complexes derived from the reaction of α‐bromo boronic esters with CF 3 SiMe 3 /KF only undergo the desired 1,2‐metallate rearrangement under forcing conditions, thus highlighting the reduced nucleophilicity of the trifluoromethyl group . Unfortunately, it is difficult to render such methodology asymmetric without the use of enzymes.…”

Development of new methods in modern selective organic synthesis: preparation of functionalized molecules with atomic precision

“…Just recently, stable organoboron compounds of this type [8, M = B(OR) 2 ] were obtained but cross-coupling reactions with these reagents have not been studied as yet. 74 Scheme 10 II.1.b. Methods for the preparation of compounds with a CF 2 group The most general approach to the formation of a CF 2 moiety is direct transformation of a carbonyl compound (aldehyde or ketone) according to the deoxofluorination reaction (Scheme 11).…”