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

T Mino, Y Naruse, S Kobayashi, S Oishi, M Sakamoto…

Index: Mino, Takashi; Naruse, Yoshiaki; Kobayashi, Shohei; Oishi, Shunsuke; Sakamoto, Masami; Fujita, Tsutomu Tetrahedron Letters, 2009 , vol. 50, # 19 p. 2239 - 2241

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Citation Number: 13

Abstract

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.