New chiral bis(oxazolinyl)bipyridine ligands and application in the iron catalyzed asymmetric hydrosilylation of ketones
DOI:
https://doi.org/10.17721/fujcV3I2P44-53Keywords:
chiral bisoxazoline, bipyridine, hydrosilylation, iron, ketonesAbstract
C2 symmetrical 6,6′-bis(oxazolinyl)-2,2′-bipyridine (bipybox) chiral ligands have been synthesized from readily available 2,2′-bipyridine. Catalytic asymmetric hydrosilylation of ketones was studied using this family of ligands in the presence of iron(II) acetate.
References
Malacea R, Poli R, Manoury E. Asymmetric hydrosilylation, transfer hydrogenation and hydrogenation of ketones catalyzed by iridium complexes. Coordination Chemistry Reviews 2010;254(5-6):729-752. https://doi.org/10.1016/j.ccr.2009.09.033
Gaillard S, Renaud J. Iron-Catalyzed Hydrogenation, Hydride Transfer, and Hydrosilylation: An Alternative to Precious-Metal Complexes?. ChemSusChem 2008;1(6):505-509. https://doi.org/10.1002/cssc.200800071
Darwish M, Wills M. Asymmetric catalysis using iron complexes – ‘Ruthenium Lite’?. Catal. Sci. Technol. 2012;2(2):243-255. https://doi.org/10.1039/c1cy00390a
Nishiyama H. 5.13 Reduction: Hydrosilylation. Comprehensive Chirality 2012;:318-333. https://doi.org/10.1016/b978-0-08-095167-6.00515-2
Zhang M, Zhang A. Iron-catalyzed hydrosilylation reactions. Appl. Organometal. Chem. 2010;24(11):751-757. https://doi.org/10.1002/aoc.1701
Roy A. A Review of Recent Progress in Catalyzed Homogeneous Hydrosilation (Hydrosilylation). Advances in Organometallic Chemistry 2007;55:1-59. https://doi.org/10.1016/s0065-3055(07)55001-x
Zhou J, Fang Q, Hu Y, Yang L, Wu F, Xie L, Wu J, Li S. Copper(ii)-catalyzed enantioselective hydrosilylation of halo-substituted alkyl aryl and heteroaryl ketones: asymmetric synthesis of (R)-fluoxetine and (S)-duloxetine. Organic & Biomolecular Chemistry 2014;12(6):1009. https://doi.org/10.1039/c3ob42214c
Qi S, Li M, Li S, Zhou J, Wu J, Yu F, Zhang X, Chan A, Wu J. Copper-dipyridylphosphine-catalyzed hydrosilylation: enantioselective synthesis of aryl- and heteroarylcycloalkyl alcohols. Org. Biomol. Chem. 2013;11(6):929-937. https://doi.org/10.1039/c2ob27040d
Sui Y, Zhang X, Wu J, Li S, Zhou J, Li M, Fang W, Chan A, Wu J. Cu II -Catalyzed Asymmetric Hydrosilylation of Diaryl- and Aryl Heteroaryl Ketones: Application in the Enantioselective Synthesis of Orphenadrine and Neobenodine . Chemistry - A European Journal 2012;18(24):7486-7492. https://doi.org/10.1002/chem.201200379
Yu F, Zhou J, Zhang X, Sui Y, Wu F, Xie L, S. C. Chan A, Wu J. Copper(II)-Catalyzed Hydrosilylation of Ketones Using Chiral Dipyridylphosphane Ligands: Highly Enantioselective Synthesis of Valuable Alcohols. Chemistry - A European Journal 2011;17(50):14234-14240. https://doi.org/10.1002/chem.201102157
Bauer I, Knölker H. Iron Catalysis in Organic Synthesis. Chemical Reviews 2015;115(9):3170-3387. https://doi.org/10.1021/cr500425u
Bolm C, Legros J, Le Paih J, Zani L. Iron-Catalyzed Reactions in Organic Synthesis. Chemical Reviews 2004;104(12):6217-6254. https://doi.org/10.1021/cr040664h
Enthaler S, Junge K, Beller M. Sustainable Metal Catalysis with Iron: From Rust to a Rising Star?. Angewandte Chemie International Edition 2008;47(18):3317-3321. https://doi.org/10.1002/anie.200800012
Misal Castro L, Li H, Sortais J, Darcel C. When iron met phosphines: a happy marriage for reduction catalysis. Green Chem. 2015;17(4):2283-2303. https://doi.org/10.1039/c4gc01866d
Bauer E. Iron Catalysis: Historic Overview and Current Trends. Topics in Organometallic Chemistry 2015;:1-18. https://doi.org/10.1007/3418_2015_107
Gopalaiah K. Chiral Iron Catalysts for Asymmetric Synthesis. Chemical Reviews 2013;113(5):3248-3296. https://doi.org/10.1021/cr300236r
Morris R. Asymmetric hydrogenation, transfer hydrogenation and hydrosilylation of ketones catalyzed by iron complexes. Chemical Society Reviews 2009;38(8):2282. https://doi.org/10.1039/b806837m
Sues P, Demmans K, Morris R. Rational development of iron catalysts for asymmetric transfer hydrogenation. Dalton Transactions 2014;43(21):7650. https://doi.org/10.1039/c4dt00612g
Fingerhut A, Serdyuk O, Tsogoeva S. Non-heme iron catalysts for epoxidation and aziridination reactions of challenging terminal alkenes: towards sustainability. Green Chem. 2015;17(4):2042-2058. https://doi.org/10.1039/c4gc02413c
Ollevier T, Keipour H. Enantioselective Iron Catalysts. Topics in Organometallic Chemistry 2015:259-309. https://doi.org/10.1007/3418_2015_102
Enthaler S. Iron Complexes as Substitutes for Toxic Metals in Asymmetric Synthesis. Comprehensive Inorganic Chemistry II 2013:549-562. https://doi.org/10.1016/b978-0-08-097774-4.00620-3
Nishiyama H, Furuta A. An iron-catalysed hydrosilylation of ketones. Chem. Commun. 2007;(7):760-762. https://doi.org/10.1039/b617388h
Inagaki T, Ito A, Ito J, Nishiyama H. Asymmetric Iron-Catalyzed Hydrosilane Reduction of Ketones: Effect of Zinc Metal upon the Absolute Configuration. Angewandte Chemie International Edition 2010;49(49):9384-9387. https://doi.org/10.1002/anie.201005363
Hosokawa S, Ito J, Nishiyama H. A Chiral Iron Complex Containing a Bis(oxazolinyl)phenyl Ligand: Preparation and Asymmetric Hydrosilylation of Ketones. Organometallics 2010;29(22):5773-5775. https://doi.org/10.1021/om1009186
Inagaki T, Phong L, Furuta A, Ito J, Nishiyama H. Iron- and Cobalt-Catalyzed Asymmetric Hydrosilylation of Ketones and Enones with Bis(oxazolinylphenyl)amine Ligands. Chemistry - A European Journal 2010;16(10):3090-3096. https://doi.org/10.1002/chem.200903118
Langlotz B, Wadepohl H, Gade L. Chiral Bis(pyridylimino)isoindoles: A Highly Modular Class of Pincer Ligands for Enantioselective Catalysis. Angewandte Chemie International Edition 2008;47(25):4670-4674. https://doi.org/10.1002/anie.200801150
Bleith T, Wadepohl H, Gade L. Iron Achieves Noble Metal Reactivity and Selectivity: Highly Reactive and Enantioselective Iron Complexes as Catalysts in the Hydrosilylation of Ketones. J. Am. Chem. Soc. 2015;137(7):2456-2459. https://doi.org/10.1021/ja512986m
Tondreau A, Darmon J, Wile B, Floyd S, Lobkovsky E, Chirik P. Enantiopure Pyridine Bis(oxazoline) “Pybox” and Bis(oxazoline) “Box” Iron Dialkyl Complexes: Comparison to Bis(imino)pyridine Compounds and Application to Catalytic Hydrosilylation of Ketones. Organometallics 2009;28(13):3928-3940. https://doi.org/10.1021/om900224e
Flückiger M, Togni A. Iron(II)-Catalyzed Asymmetric Hydrosilylation of Acetophenone. European Journal of Organic Chemistry 2011;2011(23):4353-4360. https://doi.org/10.1002/ejoc.201100550
Shaikh N, Enthaler S, Junge K, Beller M. Iron-Catalyzed Enantioselective Hydrosilylation of Ketones. Angewandte Chemie International Edition 2008;47(13):2497-2501. https://doi.org/10.1002/anie.200705624
Zuo Z, Zhang L, Leng X, Huang Z. Iron-catalyzed asymmetric hydrosilylation of ketones. Chem. Commun. 2015;51(24):5073-5076. https://doi.org/10.1039/c5cc00612k
Nishiyam H, Yamaguchi S, Park S, Itoh K. New chiral bis(oxazolinyl)bipyridine ligand (bipymox): Enantioselection in the asymmetric hydrosilylation of ketones. Tetrahedron: Asymmetry 1993;4(1):143-150. https://doi.org/10.1016/s0957-4166(00)86024-3
Zhang D, Telo J, Liao C, Hightower S, Clennan E. Experimental and Computational Studies of Nuclear Substituted 1,1‘-Dimethyl-2,2‘-Bipyridinium Tetrafluoroborates. J. Phys. Chem. A 2007;111(51):13567-13574. https://doi.org/10.1021/jp074323u
Sharmoukh W, Allam N. TiO 2 Nanotube-Based Dye-Sensitized Solar Cell Using New Photosensitizer with Enhanced Open-Circuit Voltage and Fill Factor . ACS Appl. Mater. Interfaces 2012;4(8):4413-4418. https://doi.org/10.1021/am301089t
Ollevier T, Plancq B. Highly enantioselective Mukaiyama aldol reaction in aqueous conditions using a chiral iron( ii ) bipyridine catalyst . Chem. Commun. 2012;48(17):2289-2291. https://doi.org/10.1039/c1cc16409k
Plancq B, Ollevier T. Iron(II)-catalyzed enantioselective meso-epoxide-opening with anilines. Chemical Communications 2012;48(32):3806. https://doi.org/10.1039/c2cc18032d
Lafantaisie M, Mirabaud A, Plancq B, Ollevier T. Iron(II)-Derived Lewis Acid/Surfactant Combined Catalysis for the Enantioselective Mukaiyama Aldol Reaction in Pure Water. ChemCatChem 2014;6(8):2244-2247. https://doi.org/10.1002/cctc.201402029
Plancq B, Lafantaisie M, Companys S, Maroun C, Ollevier T. Highly enantioselective iron(ii)-catalyzed opening reaction of aromatic meso-epoxides with indoles. Organic & Biomolecular Chemistry 2013;11(43):7463. https://doi.org/10.1039/c3ob41782d
Lou S, Fu G. Synthesis of Chiral Pyridine Bis(Oxazoline) Ligands for Nickel-Catalyzed Asymmetric Negishi Cross-Couplings of Secondary Allylic Chlorides with Alkylzincs: 2,6-Bis[(4 R )-4,5-Dihydro-4- (2-Phenylethyl)-2-Oxazolyl]- Pyridine . Organic Syntheses 2010;:310-316. https://doi.org/10.1002/0471264229.os087.33
Downloads
Published
Issue
Section
License
Copyright (c) 2015 French-Ukrainian Journal of Chemistry
This work is licensed under a Creative Commons Attribution 4.0 International License.
The French‑Ukrainian Journal of Chemistry holds copyright and publishes all articles under a Creative Commons Attribution 4.0 International licence (CC BY 4.0).
This license permits unrestricted use, sharing, adaptation, distribution, and reproduction in any medium or format, provided that the original author(s) and source are credited, a link to the license is included, and any changes made are indicated.
Authors grant the French‑Ukrainian Journal of Chemistry the exclusive right of first publication and may enter into separate, non‑exclusive distribution agreements for the published version (e.g., institutional repository, book chapter). Authors are also encouraged to post pre‑prints and post‑prints online to increase visibility and citation.
