Cellulose-supported chiral Rh nanoparticle (NP) catalysts have been developed. The Rh NPs, which were well dispersed on cellulose, catalyzed the asymmetric 1,4-addition of arylboronic acids to enones and enoates, one of the representative asymmetric carbon-carbon bond-forming reactions, in the presence of chiral diene ligands, providing the corresponding adducts in high yields with outstanding enantioselectivities without metal leaching. The solid-state NMR analysis of the chiral NP system directly suggested interactions between the Rh NPs and the chiral ligand on cellulose. This is the first example of using polysaccharide-supported chiral metal nanoparticles for asymmetric carbon-carbon bond-forming reactions.
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| http://dx.doi.org/10.1039/c5sc02510a | DOI Listing |
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Article Synopsis
- The study demonstrates that the addition of arylboronic acids to aryl(alkyl)alkynes can preferentially form 1,1-diarylalkenes (α-addition) when using a rhodium catalyst with a chiral diene ligand.
- The typical reaction produces carbon-carbon bonds at the alkyl-substituted carbon (β-addition) with a different rhodium/DM-BINAP catalyst, highlighting how ligand choice affects regioselectivity.
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