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Organic Solvent‐free Asymmetric 1,4‐Addition in Liquid‐ or Solid‐State using Conventional Stirring Catalyzed by a Chiral Rhodium Complex Developed as a Homogeneous Catalyst
Author(s) -
Korenaga Toshinobu,
Kori Hiroto,
Asai Shota,
Kowata Ryo,
Shirai Masayuki
Publication year - 2020
Publication title -
chemcatchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.497
H-Index - 106
eISSN - 1867-3899
pISSN - 1867-3880
DOI - 10.1002/cctc.202001479
Subject(s) - catalysis , rhodium , adduct , chemistry , solvent , yield (engineering) , organic chemistry , homogeneous catalysis , materials science , metallurgy
Organic solvent‐free asymmetric 1,4‐addition of arylboronic acids to enone substrates was performed by using a chiral rhodium complex catalyst developed as a homogeneous catalyst. Reactions catalyzed by [RhOH(cod)] 2 with chiral diphosphine ligands in liquid‐ or solid‐state proceeded to give chiral 1,4‐adducts in high yield with enantioselectivities up to ca. 100 % ee by conventional stirring without mechanochemistry such as ball milling. The solid‐state reactions under a static condition also proceeded, but with a slight decrease in enantioselectivity of the 1,4‐adduct. SEM observations of the solid‐state reactions indicated that no nanoparticles catalyst was generated. The organic solvent‐free reaction could be applied to gram‐scale synthesis by performing a greener purification using a minimum necessary organic solvent.