Potassium Methyltrifluoroborate

Robust and General Late-Stage Methylation of Aryl Chlorides: Application to Isotopic Labeling of Drug-like Scaffolds

“…To begin to address the challenges outlined above, we proposed that potassium methyltrifluoroborate had the potential to be an ideal reagent for the isotopically labeled late-stage methylation of aryl chlorides. In particular, as an easy-to-handle, free-flowing solid, this species possesses the key properties that would allow for facile use even under the more rigorous requirements within radiochemical laboratories. In addition, organotrifluoroborate salts have emerged as versatile reagents in cross-coupling and their use for the alkylation of aryl chlorides has previously been demonstrated by Molander and co-workers .…”

Brush-First and ROMP-Out with Functional (Macro)monomers: Method Development, Structural Investigations, and Applications of an Expanded Brush-Arm Star Polymer Platform

“…Nickel-catalyzed Miyaura borylation 38 of readily accessible 4-chlorobenzyl(N-Boc-amine) with tetrahydroxydiboron afforded the putative arylboronic acid, which was deprotected with TFA to afford Cap-B(OH) 2 in 34% yield over three steps. Treatment of crude 7-20-7-2PNP and 10-10-10-2PNP with excess Cap-B(OH) 2 (5 equiv relative to Nb-PNP used) and DIPEA (5 equiv) in 1:1 1,4-dioxane/DMSO afforded boronic acid-functionalized BASPs 7-20-7-2BA and 10-10-10-2BA with >92% conversion within 48 h based on HPLC analysis of p-nitrophenol production (Figure S15 and Table S1).…”