Synthesis and application of atropisomeric dihydrobenzofuran-based bisphosphine (BICMAP)

A new atropisomeric dihydrobenzofuran-based bisphosphine ligand 1 was easily prepared from 1,4-dibromo-2-fluorobenzene. This racemic bisphosphine (±)-1 was used as a ligand for the palladium-catalyzed Suzuki–Miyaura reaction of aryl chloride with arylboronic acids and Hartwig–Buchwald amination of aryl bromides with aniline derivatives. The optical resolution of (±)-1 was also carried out by HPLC with a chiral stationary phase column.