Issue 12, 2015

The first chiral diene-based metal–organic frameworks for highly enantioselective carbon–carbon bond formation reactions

Abstract

We have designed the first chiral diene-based metal–organic framework (MOF), E2-MOF, and postsynthetically metalated E2-MOF with Rh(I) complexes to afford highly active and enantioselective single-site solid catalysts for C–C bond formation reactions. Treatment of E2-MOF with [RhCl(C2H4)2]2 led to a highly enantioselective catalyst for 1,4-additions of arylboronic acids to α,β-unsaturated ketones, whereas treatment of E2-MOF with Rh(acac)(C2H4)2 afforded a highly efficient catalyst for the asymmetric 1,2-additions of arylboronic acids to aldimines. Interestingly, E2-MOF·Rh(acac) showed higher activity and enantioselectivity than the homogeneous control catalyst, likely due to the formation of a true single-site catalyst in the MOF. E2-MOF·Rh(acac) was also successfully recycled and reused at least seven times without loss of yield and enantioselectivity.

Graphical abstract: The first chiral diene-based metal–organic frameworks for highly enantioselective carbon–carbon bond formation reactions

Supplementary files

Article information

Article type
Edge Article
Submitted
10 Jun 2015
Accepted
14 Sep 2015
First published
14 Sep 2015
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2015,6, 7163-7168

Author version available

The first chiral diene-based metal–organic frameworks for highly enantioselective carbon–carbon bond formation reactions

T. Sawano, P. Ji, A. R. McIsaac, Z. Lin, C. W. Abney and W. Lin, Chem. Sci., 2015, 6, 7163 DOI: 10.1039/C5SC02100F

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