2025/01/01 by Akifumi Sumida, Kaisei Yamamoto, Takahiro Iwamoto +2 · 1 voice
Chemistry · #Organic Chemistry Cycloaddition Reactions #Chemical Synthesis and Reactions #Chemical Reaction Mechanisms
paper · pdf · doi:10.1039/d5sc05285h
openalex publication_date 2025/01/01 · openalex created_date 2025/10/21 · openalex updated_date 2026/07/28
has not been explored. In this study, the steric and electronic requirements of the Pd-catalyzed C-H difunctionalization of thiophene are explored using 36 synthesized arsines and nine phosphines. Ligand parameterization reveals that arsines with moderate electron-donating abilities and sufficient steric accessibility were preferred. Notably, the identified steric demand is more readily met by arsines than by phosphines. Furthermore, arsines exhibit superior oxidative stability under reaction conditions that typically oxidize phosphines owing to the high oxophilicity of phosphorus. These experimental and computational findings demonstrate that the use of arsines can expand the scope of transition metal catalysts by enabling access to catalytic spaces that are less accessible with traditional phosphines.