Synthesis and Application of Diaryl Ether-Derived Monodentate Phosphine Ligands for the Pd-Catalyzed Arylation of Amines

Qicai Ma; Wenjing Wang; Cong Fu; Shanyue Li; Wei Zhou

doi:10.1055/a-2608-2226

Synlett, Table of Contents

Synlett
DOI: 10.1055/a-2608-2226

letter

Synthesis and Application of Diaryl Ether-Derived Monodentate Phosphine Ligands for the Pd-Catalyzed Arylation of Amines

Authors

Qicai Ma

¹International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education, College of Pharmacy, Jinan University, Guangzhou, China
Wenjing Wang

¹International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education, College of Pharmacy, Jinan University, Guangzhou, China
Cong Fu

¹International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education, College of Pharmacy, Jinan University, Guangzhou, China
Shanyue Li

¹International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education, College of Pharmacy, Jinan University, Guangzhou, China
Wei Zhou

¹International Cooperative Laboratory of Traditional Chinese Medicine Modernization and Innovative Drug Development of Chinese Ministry of Education, College of Pharmacy, Jinan University, Guangzhou, China

Abstract

All articles of this category

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.

Keywords

Diaryl ether - Phosphine ligand - Pd-catalyzed - C–N coupling - Amine

Full Text

References

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

Supplementary Material

Supplementary Material (PDF)