Metal-free catalytic hydrogenation of polar substrates by frustrated Lewis pairs
- PMID: 21534552
- DOI: 10.1021/ic200663v
Metal-free catalytic hydrogenation of polar substrates by frustrated Lewis pairs
Abstract
In 2006, our group reported the first metal-free systems that reversibly activate hydrogen. This finding was extended to the discovery of "frustrated Lewis pair" (FLP) catalysts for hydrogenation. It is this catalysis that is the focal point of this article. The development and applications of such FLP hydrogenation catalysts are reviewed, and some previously unpublished data are reported. The scope of the substrates is expanded. Optimal conditions and functional group tolerance are considered and applied to targets of potential commercial significance. Recent developments in asymmetric FLP hydrogenations are also reviewed. The future of FLP hydrogenation catalysts is considered.
© 2011 American Chemical Society
Similar articles
-
Catalytic hydrogenation with frustrated Lewis pairs: selectivity achieved by size-exclusion design of Lewis acids.Chemistry. 2012 Jan 9;18(2):574-85. doi: 10.1002/chem.201102438. Epub 2011 Dec 12. Chemistry. 2012. PMID: 22161804
-
Frustrated Lewis pairs: from concept to catalysis.Acc Chem Res. 2015 Feb 17;48(2):306-16. doi: 10.1021/ar500375j. Epub 2014 Dec 23. Acc Chem Res. 2015. PMID: 25535796
-
"Frustrated Lewis pair" hydrogenations.Org Biomol Chem. 2012 Aug 14;10(30):5740-6. doi: 10.1039/c2ob25339a. Epub 2012 Apr 16. Org Biomol Chem. 2012. PMID: 22505184
-
FLP catalysis: main group hydrogenations of organic unsaturated substrates.Chem Soc Rev. 2019 Jul 1;48(13):3592-3612. doi: 10.1039/c8cs00277k. Chem Soc Rev. 2019. PMID: 30178796 Review.
-
Frustrated Lewis Pairs in Heterogeneous Catalysis: Theoretical Insights.Molecules. 2022 Jun 10;27(12):3734. doi: 10.3390/molecules27123734. Molecules. 2022. PMID: 35744860 Free PMC article. Review.
Cited by
-
Triphenylborane in Metal-Free Catalysis.Molecules. 2023 Jan 31;28(3):1340. doi: 10.3390/molecules28031340. Molecules. 2023. PMID: 36771006 Free PMC article. Review.
-
Versatile Catalytic Hydrogenation Using A Simple Tin(IV) Lewis Acid.Angew Chem Int Ed Engl. 2016 Nov 14;55(47):14738-14742. doi: 10.1002/anie.201606639. Epub 2016 Oct 24. Angew Chem Int Ed Engl. 2016. PMID: 27774711 Free PMC article.
-
Water Reduction and Dihydrogen Addition in Aqueous Conditions With ansa-Phosphinoborane.Chemistry. 2022 Nov 2;28(61):e202201927. doi: 10.1002/chem.202201927. Epub 2022 Aug 31. Chemistry. 2022. PMID: 35861909 Free PMC article.
-
Incorporation of Chiral Frustrated Lewis Pair into Metal-Organic Framework with Tailored Microenvironment for Heterogeneous Enantio- and Chemoselective Hydrogenation.ACS Cent Sci. 2023 Jul 27;9(8):1692-1701. doi: 10.1021/acscentsci.3c00637. eCollection 2023 Aug 23. ACS Cent Sci. 2023. PMID: 37637733 Free PMC article.
-
A frustrated-Lewis-pair approach to catalytic reduction of alkynes to cis-alkenes.Nat Chem. 2013 Aug;5(8):718-23. doi: 10.1038/nchem.1693. Epub 2013 Jul 7. Nat Chem. 2013. PMID: 23881505
LinkOut - more resources
Full Text Sources
Other Literature Sources