Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Download PDF
Synthesis
DOI: 10.1055/a-2675-3869
DOI: 10.1055/a-2675-3869
Paper
Published as part of the Special Topic Dedicated to Prof. Paul Knochel
Synthesis of Symmetric and P-Stereogenic Self-Assembling Pyridone-Based Phosphorus Ligands
Supported by: Albert-Ludwigs Universität
Dedication
Dedicated to Paul Knochel on the occasion of his 70th birthday.
Abstract
6-(Diphenylphosphino)pyridin-2(1H)-one (6-DPPon) is a unique ligand that can self-assemble in transition metal complexes. This self-assembly is achieved through hydrogen bonding interactions that mimic a bidentate coordination sphere. As a consequence, there is considerable interest in preparing derivatives of 6-DPPon and optimizing their synthesis. Herein, we present different methods for the preparation of self-assembling pyridone-based phosphorus ligands. Nineteen pyridone ligands were prepared using electrophilic and nucleophilic routes, including eleven P-stereogenic ligands.
Keywords
Ligand synthesis - Pyridone ligands - Self-assembly - P-stereogenic ligands - Phosphine chlorides - Bromine–lithium exchange - Crystal structurePublication History
Received: 17 June 2025
Accepted after revision: 03 August 2025
Accepted Manuscript online:
03 August 2025
Article published online:
12 September 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1 Breit B, Seiche W. J Am Chem Soc 2003; 125: 6608-6609
- 2 Gellrich U, Koslowski T, Breit B. Catal Sci Technol 2015; 5: 129-133
- 3 Gellrich U, Himmel D, Meuwly M, Breit B. Chem Eur J 2013; 19: 16272-16281
- 4 Gellrich U, Seiche W, Keller M, Breit B. Angew Chem Int Ed 2012; 51: 11033-11038
- 5 Huang J, Häussinger D, Gellrich U, Seiche W, Breit B, Meuwly M. J Phys Chem B 2012; 116: 14406-14415
- 6 Gellrich U, Huang J, Seiche W, Keller M, Meuwly M, Breit B. J Am Chem Soc 2011; 133: 964-975
- 7 Seiche W, Schuschkowski A, Breit B. Adv Synth Catal 2005; 347: 1488-1494
- 8 Straub AT, Otto M, Usui I, Breit B. Adv Synth Catal 2013; 355: 2071-2075
- 9 Spang J, Bork H, Belov F, Langermann J v, Vorholt AJ, Gröger H. Org Biomol Chem 2025; 23: 688-692
- 10 Manske JL, Nicolai J, Bloomer BJ, Clark DS, Hartwig JF. ACS Catal 2024; 14: 14356-14362
- 11 Bork H, Naße KE, Vorholt AJ, Gröger H. Angew Chem Int Ed 2024; 63: e202401989
- 12 Fuchs D, Rousseau G, Diab L, Gellrich U, Breit B. Angew Chem Int Ed 2012; 51: 2178-2182
- 13 Abillard O, Breit B. Adv Synth Catal 2007; 349: 1891-1895
- 14 Miller L, Bauer F, Breit B. Chem Eur J 2024; 30: e202400188
- 15 Miller L, Bauer F, Breit B. Eur J Org Chem 2025; 28: e202401089
- 16 Miller L, Impelmann A, Bauer F, Breit B. Chem Eur J 2024; 30: e202303752
- 17 Kemme ST, Smejkal T, Breit B. Chem Eur J 2010; 16: 3423-3433
- 18 Köpfer A, Breit B. Angew Chem Int Ed 2015; 54: 6913-6917
- 19 Agabekov V, Seiche W, Breit B. Chem Sci 2013; 4: 2418-2422
- 20 Wenz KM, Leonhardt-Lutterbeck G, Breit B. Angew Chem Int Ed 2018; 57: 5100-5104
- 21 Usui I, Schmidt S, Keller M, Breit B. Org Lett 2008; 10: 1207-1210
- 22a Birkholz M-N, Dubrovina NV, Shuklov IA. et al. Tetrahedron Asymmetry 2007; 18: 2055-2060
- 22b The synthesis of 1 is also possible using only HNEt2. See the following reference Issleib K, Seidel W. Chem Ber 1959; 92: 2681-2694
- 22c For the positive effects of tertiary amine bases in the addition of secondary amines to phosphorus chlorides see: Moloy KG, Petersen JL. J Am Chem Soc 1995; 117: 7696-7710
- 22d Amigues EJ, Hardacre C, Keane G, Migaud ME. Green Chem 2008; 10: 660-669
- 23 Kraushaar K, Herbig M, Schmidt D, Wagler J, Böhme U, Kroke E. Z Naturforsch B 2017; 72: 909-921
- 24 Dellinger DJ, Sheehan DM, Christensen NK, Lindberg JG, Caruthers MH. J Am Chem Soc 2003; 125: 940-950
- 25 Bestmann HJ, Lienert J, Heid E. Chem Ber 1982; 115: 3875-3879
- 26 Burg AB, Slota PJ. J Am Chem Soc 1958; 80 (05) 1107-1109
- 27 Chantrell PG, Pearce CA, Toyer CR, Twaits R. J Appl Chem 1964; 14: 563-564
- 28 Hunt BB, Saunders BC. J Chem Soc 1957; 2413-2432
- 29 Nöth H, Vetter H-J. Chem Ber 1963; 96: 1109-1118
- 30 Montgomery RE, Quin LD. J Org Chem 1965; 30: 2393-2395
- 31 Casalnuovo AL, RajanBabu TV, Ayers TA, Warren TH. J Am Chem Soc 1994; 116: 9869-9882
- 32 Trost BM, Marschner C. Bull Soc Chim Fr 1997; 263-274
- 33 Zhang J-Q, Yang S, Han L-B. Tetrahedron Lett 2020; 61: 151556
- 34 Fogh AA, Belazregue S, Ashley AE, Chadwick FM. Organometallics 2025; 44: 665-671
- 35 Allmendinger S, Kinuta H, Breit B. Adv Synth Catal 2015; 357: 41-45
- 36 Reiter SA, Nogai SD, Schmidbaur H. Dalton Trans 2005; 247-255
- 37 Bauer F, Dierenbach N, Breit B, Asian J. Org Chem 2023; 12: e202300244
- 38 Pudovik MAZ. Obshch Khim 1981; 51: 518-526
- 39 Prikoszovich W, Schindlbauer H. Chem Ber 1969; 102 (09) 2922-2929
- 40 Imamoto T, Oshiki T, Onozawa T, Kusumoto T, Sato K. J Am Chem Soc 1990; 112: 5244-5252
- 41 Diebolt O, Tricas H, Freixa Z, van Leeuwen PWNM. ACS Catal 2013; 3: 128-137
- 42 Suffert J. J Org Chem 1989; 54: 509-510
- 43 Love BE, Jones EG. J Org Chem 1999; 64: 3755-3756
- 44 Landis MS, Turro NJ, Bhanthumnavin W, Bentrude WG. J Organomet Chem 2002; 646: 239-246
- 45 Czauderna CF, Slawin AMZ, Cordes DB, van der Vlugt JI, Kamer PCJ. Tetrahedron 2019; 75: 47-56
- 46 Stoop RM, Mezzetti A, Spindler F. Organometallics 1998; 17 (04) 668-675
- 47 Lee H, Hong SH. Appl Catal A Gen 2018; 560: 21-27
- 48 Kapoor PN, Pathak DD, Gaur G, Kutty M. J Organomet Chem 1984; 276: 167-170
- 49 Lhermet R, Moser E, Jeanneau E, Olivier-Bourbigou H, Breuil P-AR. Chem Eur J 2017; 23: 7433-7437