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Biaryl-Like CATPHOS Diphosphines via Double Diels–Alder Cycloaddition between 1,4-Bis(diphenylphosphinoyl)buta-1,3-diyne and Anthracenes: Efficient Ligands for the Palladium-Catalyzed Amination of Aromatic Bromides and α-Arylation of Ketones

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School of Natural Sciences, Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne NE1 7RU, U.K.
Cite this: Organometallics 2008, 27, 8, 1679–1682
Publication Date (Web):March 26, 2008
https://doi.org/10.1021/om800118t
Copyright © 2008 American Chemical Society

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    Abstract

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    A mixture of palladium(0) and CATPHOS, the 1,3-butadiene-bridged diphosphine generated via double Diels–Alder cycloaddition between bis(diphenylphosphinoyl)buta-1,3-diyne and anthracene, catalyzes the amination of a range of aromatic bromides as well as the α-arylation of ketones, giving conversions that either rival or exceed those obtained with BINAP.

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    Text, figures, a table, and CIF files giving full details of experimental procedures and characterization data for all compounds, details of catalyst testing, and, for compounds 4, 5a,b, and 7, details of crystal data, structure solution and refinement, atomic coordinates, bond distances, bond angles, anisotropic displacement parameters. This material is available free of charge via the Internet at http://pubs.acs.org.

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    This article is cited by 20 publications.

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    2. Fabio Bellina and Renzo Rossi. Transition Metal-Catalyzed Direct Arylation of Substrates with Activated sp3-Hybridized C−H Bonds and Some of Their Synthetic Equivalents with Aryl Halides and Pseudohalides. Chemical Reviews 2010, 110 (2) , 1082-1146. https://doi.org/10.1021/cr9000836
    3. Simon Doherty, Catherine H. Smyth, Ross W. Harrington and William Clegg. Synthesis of Biaryl Diphosphines via a Stepwise Regioselective Double Diels−Alder Cycloaddition−Elimination Sequence: Efficient Ligands for the Palladium-Catalyzed Amination of Aromatic Bromides. Organometallics 2009, 28 (17) , 5273-5276. https://doi.org/10.1021/om9004862
    4. Simon Doherty, Catherine H. Smyth, Anthony Harriman, Ross W. Harrington and William Clegg. Can a Butadiene-Based Architecture Compete with its Biaryl Counterpart in Asymmetric Catalysis? Enantiopure Me-CATPHOS, a Remarkably Efficient Ligand for Asymmetric Hydrogenation. Organometallics 2009, 28 (3) , 888-895. https://doi.org/10.1021/om801145v
    5. Wenbo Li, Junliang Zhang. Design and synthesis of typical chiral bisphosphorus ligands. 2023, 1-65. https://doi.org/10.1016/B978-0-323-85225-8.00008-3
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    7. Yasushi Obora. C-Alkylation by Hydrogen Autotransfer Reactions. Topics in Current Chemistry 2016, 374 (2) https://doi.org/10.1007/s41061-016-0012-8
    8. . Synthesis of Organophosphines, Phosphonates, and Related Compounds. 2016, 219-470. https://doi.org/10.1002/9781119015789.ch4
    9. . α‐Arylation Processes. 2014, 376-435. https://doi.org/10.1002/9783527672707.ch8
    10. Bin Li, Christophe Darcel, Pierre H. Dixneuf. sp 3 C–H bond alkylation of ketones with alkenes via ruthenium( ii ) catalysed dehydrogenation of alcohols. Chem. Commun. 2014, 50 (45) , 5970-5972. https://doi.org/10.1039/C4CC00931B
    11. T. Kégl, L. Kollár. Chiral Phosphorous Ligands in Asymmetric Catalysis. 2013, 271-308. https://doi.org/10.1016/B978-0-08-097774-4.00613-6
    12. Simon Doherty, Catherine H Smyth, Julian G Knight, Stephen A K Hashmi. Synthesis of an electron-rich KITPHOS monophosphine, preparation of derived metal complexes and applications in catalysis. Nature Protocols 2012, 7 (10) , 1870-1883. https://doi.org/10.1038/nprot.2012.107
    13. Simon Doherty, Catherine H Smyth. Synthesis and resolution of the biaryl-like diphosphine (S)-Me2-CATPHOS, preparation of a derived rhodium precatalyst and applications in asymmetric hydrogenation. Nature Protocols 2012, 7 (10) , 1884-1896. https://doi.org/10.1038/nprot.2012.108
    14. Simon Doherty, Julian G. Knight, Hamid Mehdi-Zodeh. Asymmetric carbonyl-ene and Friedel–Crafts reactions catalysed by Lewis acid platinum group metal complexes of the enantiopure atropisomeric biaryl-like diphosphine (S)-Me2-CATPHOS: a comparison with BINAP. Tetrahedron: Asymmetry 2012, 23 (3-4) , 209-216. https://doi.org/10.1016/j.tetasy.2012.01.022
    15. Georgia S. Lemen, John P. Wolfe. Palladium-Catalyzed sp2 C–N Bond Forming Reactions: Recent Developments and Applications. 2012, 1-53. https://doi.org/10.1007/3418_2012_56
    16. Azusa Kondoh, Hideki Yorimitsu, Koichiro Oshima. 1‐Alkynylphosphines and Their Derivatives as Key Starting Materials in Creating New Phosphines. Chemistry – An Asian Journal 2010, 5 (3) , 398-409. https://doi.org/10.1002/asia.200900447
    17. Simon Doherty, Julian G. Knight, John P. McGrady, Alexandra M. Ferguson, Nicholas A. B. Ward, Ross W. Harrington, William Clegg. ortho,ortho′ ‐Substituted KITPHOS Monophosphines: Highly Efficient Ligands for Palladium‐Catalyzed CC and CN Bond Formation. Advanced Synthesis & Catalysis 2010, 352 (1) , 201-211. https://doi.org/10.1002/adsc.200900577
    18. Cédric Bouteiller, Javier Becerril-Ortega, Patrice Marchand, Olivier Nicole, Louisa Barré, Alain Buisson, Cécile Perrio. Copper-catalyzed amination of (bromophenyl)ethanolamine for a concise synthesis of aniline-containing analogues of NMDA NR2B antagonist ifenprodil. Organic & Biomolecular Chemistry 2010, 8 (5) , 1111. https://doi.org/10.1039/b923255a
    19. Simon Doherty, Julian G. Knight, Catherine H. Smyth, Ross W. Harrington, William Clegg. ChemInform Abstract: Biaryl‐Like CATPHOS Diphosphines via Double Diels—Alder Cycloaddition Between 1,4‐Bis(diphenylphosphinoyl)buta‐1,3‐diyne and Anthracenes: Efficient Ligands for the Palladium‐Catalyzed Amination of Aromatic Bromides and α‐Arylation of Ketones.. ChemInform 2008, 39 (34) https://doi.org/10.1002/chin.200834039
    20. Simon Doherty, Julian G. Knight, Catherine H. Smyth, Graeme A. Jorgenson. Electron‐Rich, Bicyclic Biaryl‐Like KITPHOS Monophosphines via [4+2] Cycloaddition between 1‐Alkynylphosphine Oxides and Anthracene: Highly Efficient Ligands for Palladium‐Catalysed CN and CC Bond Formation. Advanced Synthesis & Catalysis 2008, 350 (11-12) , 1801-1806. https://doi.org/10.1002/adsc.200800307

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