2026/04/03 by Ryan Harbit, Luiz Paulo Melchior de Oliveira Leão, Serhii V. Korobko +4 · 1 voice
Chemistry · #Catalytic Cross-Coupling Reactions #Organoboron and organosilicon chemistry #Catalytic C–H Functionalization Methods
paper · pdf · doi:10.26434/chemrxiv.15001572/v1
openalex publication_date 2026/04/03 · openalex created_date 2026/04/04 · openalex updated_date 2026/07/15
A mild, efficient, and practical method for the methylation of aryl bromides and triflates utilizing activated boronate nucleophiles is described. The mildness of this cross-coupling reaction relies on the unique utilization of a preactivated, but stable mixed lithium dialkyl boronate salt that displays high reactivity and selectivity in B-alkyl Suzuki coupling events. The reaction requires no exogenous hydroxide or alkoxide base, rendering it tolerant of substrates that would typically undergo degradation under canonical Suzuki alkylation events. Amidst a broad scope that includes the late-stage methylation of natural products and drug scaffolds, this reaction also improves upon tactically similar Suzuki alkylations that suffer from low yields and/or conversion. In addition, applications in isotopic labeling were explored along with a high-throughput substrate screening assay that further unveils the breadth of this transformation, demonstrating the immense potential for these unique nucleophiles in programmatic cross-coupling.