RSS-Feed abonnieren
DOI: 10.1055/a-2608-2226
Synthesis and Application of Diaryl Ether-Derived Monodentate Phosphine Ligands for the Pd-Catalyzed Arylation of Amines
Gefördert durch: Central University Basic Research Fund of China 21624403
Funding Information The authors are grateful to the Fundamental Research Funds for Central Universities (21624403) for their financial support.

Abstract
A set of diaryl ether-derived monodentate phosphine ligands (DAE-Phos) are reported, which can be easily synthesized from readily available starting materials. In contrast to the dialkyl-ortho-biaryl class of phosphines, commonly known as Buchwald-type ligands, DAE-Phos bears a more flexible diaryl ether side chain. With the Pd/L7 catalyst, a wide range of (hetero)aryl chloride coupled well with amines under 1 mol% catalyst loading and solvent-free condition.
Publikationsverlauf
Eingereicht: 06. April 2025
Angenommen nach Revision: 14. Mai 2025
Accepted Manuscript online:
14. Mai 2025
Artikel online veröffentlicht:
28. Juli 2025
© 2025. Thieme. All rights reserved.
Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany
-
References
- 1a Vitaku E, Smith DT, Njardarson JT. J Med Chem 2014; 57: 10257-10274
- 1b Roughley SD, Jordan AM. J Med Chem 2011; 54: 3451-3479
- 1c Schneider N, Lowe DM, Sayle RA, Tarselli MA, Landrum G. J Med Chem 2016; 59: 4385-4402
- 1d Brown DG, Bostrom J. J Med Chem 2016; 59: 4443-4458
- 1e Devendar P, Qu R-Y, Kang W-M, He B, Yang G-F. J Agric Food Chem 2018; 66: 8914-8934
- 2 For a review see: Ruiz-Castillo P, Buchwald SL. Chem Rev 2016; 116: 12564-12649
- 3a Borzenko A, Rotta-Loria NL, MacQueen PM. et al. Angew Chem Int Ed 2015; 54: 3773-3777
- 3b Lavoie CM, MacQueen PM, Stradiotto M. Chem Eur J 2016; 22: 18752-18755
- 3c Tassone JP, MacQueen PM, Lavoie M. et al. ACS Catal 2017; 7: 6048-6059
- 4a For selected reviews, see: Shaughnessy KH, Ciganek E, DeVasher RB. Org React 2014; 1-668
- 4b Evano G, Blanchard N, Toumi M. Chem Rev 2008; 108: 3054-3131
- 5a Louie J, Hartwig JF. Tetrahedron Lett 1995; 36: 3609-3612
- 5b Guranm AS, Rennels RA, Buchwald SL. Angew Chem Int Ed 1995; 34: 1348-1350
- 5c Surry DS, Buchwald SL. Angew Chem Int Ed 2008; 47: 6338-6361
- 5d Surry DS, Buchwald SL. Chem Sci 2011; 2: 27-50
- 6 Ingoglia BT, Wagen CC, Buchwald SL. Tetrahedron 2019; 75: 4199-4211
- 7 Barder TE, Walker SD, Martinelli JR, Buchwald SL. J Am Chem Soc 2005; 127: 4685-4696
- 8 Milne JE, Buchwald SL. J Am Chem Soc 2004; 126: 13028
- 9 Huang X, Anderson KW, Zim D. et al. J Am Chem Soc 2003; 125: 6653-6655
- 10a Wu X, Fors BP, Buchwald SL. Angew Chem Int Ed 2011; 50: 9943-9947
- 10b Sather AC, Lee HG, De La Rosa VY. et al. J Am Chem Soc 2015; 137: 13433-13438
- 10c Sather AC, Buchwald SL. Acc Chem Res 2016; 49: 2146-2157
- 10d Watson DA, Su M, Teverovskiy G. et al. Science 2009; 325: 1661-1664
- 10e Milner PJ, Kinzel T, Zhang Y, Buchwald SL. J Am Chem Soc 2014; 136: 15757-15766
- 11a Fors BP, Watson DA, Biscoe MR, Buchwald SL. J Am Chem Soc 2008; 130: 13552-13554
- 11b Feng K, Raguram ER, Howard JR. et al. J Am Chem Soc 2024; 146 (39) 26609-26615
- 12a Nicolaou KC, Boddy CNC. J Am Chem Soc 2002; 124: 10451-10455
- 12b Duggan BM, Craik DJ. J Med Chem 1997; 40: 2259-2265
- 12c Crowley BM, Boger DL. J Am Chem Soc 2006; 128: 2885-2892
- 12d Zdrazil B, Guha R. J Med Chem 2018; 61: 4688-4703
- 12e Chen T, Xiong H, Yang J-F. et al. J Agric Food Chem 2020; 68: 9839-9877
- 13 Kranenburg M, van der Burgt YEM, Kamer PCJ. et al. Organometallics 1995; 14: 3081-3089
- 14 Guari Y, van Es DS, Reek JNH, Kamer PCJ, van Leeuwen PWNM. Tetrahedron Lett 1999; 40: 3789-3790
- 15 Chen H, Han J, Wang L. Angew Chem Int Ed 2018; 57: 12313-12317
- 16 L1–L3 are air and moisture stable; L4–L7 should be stored under oxygen free condition since they are partially oxidized when exposed to air for one week at room temperature.
- 17 Schuster C, Börger C, Julich-Gruner KK. et al. Eur J Org Chem 2014; 4741-4752
- 18 Niculescu-Duvaz I, Roman E, Whittaker SR. et al. J Med Chem 2008; 51: 3261-3274
- 19 Xu H, Li X, Hao H. et al. Appl Catal B Environ 2011; 285: 119796-119806