Synthesis 2017; 49(11): 2337-2350
DOI: 10.1055/s-0036-1589498
short review
© Georg Thieme Verlag Stuttgart · New York

The Role of PEG on Pd- and Cu-Catalyzed Cross-Coupling Reactions

Marina J. D. Pires
[email protected], Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal   Email: [email protected]
,
Sara I. Purificação
[email protected], Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal   Email: [email protected]
,
A. Sofia Santos
[email protected], Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal   Email: [email protected]
,
M. Manuel B. Marques*
[email protected], Departamento de Química, Faculdade de Ciências e Tecnologia, Universidade Nova de Lisboa, Campus de Caparica, 2829-516 Caparica, Portugal   Email: [email protected]
› Author Affiliations
Further Information

Publication History

Received: 25 January 2017

Accepted after revision: 06 March 2017

Publication Date:
26 April 2017 (online)


Abstract

Carbon–carbon and carbon–heteroatom coupling reactions are among the most important transformations in organic synthesis as they enable complex structures to be formed from readily available compounds under different routes and conditions. Several metal-catalyzed cross-coupling reactions have been developed creating many efficient methods accessible for the direct formation of new bonds between differently hybridized carbon atoms.

During the last decade, much effort has been devoted towards improvement of the sustainability of these reactions, such as catalyst recovery and atom efficiency. Polyethylene glycol (PEG) can be used as a medium, as solid-liquid phase transfer catalyst, or even as a polymer support. PEG has been investigated in a wide variety of cross-coupling reactions either as an alternative solvent to the common organic solvents or as a support for catalyst, substrate, and ligand. In this review we will summarize the different roles of PEG in palladium- and copper-catalyzed cross-coupling reactions, with the focus on Heck, Suzuki–Miyaura, Sonogashira, Buchwald–Hartwig, Stille, Fukuyama, and homocoupling reactions. We will highlight the role of PEG, the preparation of PEGylated catalysts and substrates, and the importance for the reaction outcome and applicability.

1 Introduction

2 PEG in Heck Reactions

3 PEG in Homocoupling Reactions

4 PEG in Suzuki–Miyaura Reactions

5 PEG in Sonogashira Reactions

6 PEG in Buchwald–Hartwig Reactions

7 PEG in Stille Reactions

8 PEG in Fukuyama Reactions

9 PEG in Miscellaneous Cross-Coupling Routes

10 Conclusions

 
  • References

  • 1 Johansson Seechurn CC. C. Kitching MO. Colacot TJ. Snieckus V. Angew. Chem. Int. Ed. 2012; 51: 5062
  • 2 Chen J. Spear SK. Huddleston JG. Rogers RD. Green Chem. 2005; 7: 64
  • 3 Colacino E. Martinez J. Lamaty F. Patrikeeva LS. Khemchyan LL. Ananikov VP. Beletskaya IP. Coord. Chem. Rev. 2012; 256: 2893
  • 4 Felpin F.-X. Nassar-Hardy L. Le Callonnec F. Fouquet E. Tetrahedron 2011; 67: 2815
  • 5 Beletskaya IP. Cheprakov AV. Chem. Rev. 2000; 100: 3009
  • 6 Franzén R. Can. J. Chem. 2000; 78: 957
  • 7 Chandrasekhar S. Narsihmulu C. Sultana SS. Reddy NR. Org. Lett. 2002; 4: 4399
  • 8 Wang L. Zhang Y. Liu L. Wang Y. J. Org. Chem. 2006; 71: 1284
  • 9 Declerck V. Ribière P. Nédellec Y. Allouchi H. Martinez J. Lamaty F. Eur. J. Org. Chem. 2007; 201
  • 10 Han W. Liu N. Liu C. Jin ZL. Chin. Chem. Lett. 2010; 21: 1411
  • 11 Ghorbani-Choghamarani A. Tahmasbi B. Moradi P. RSC Adv. 2016; 6: 43205
  • 12 Luo C. Zhang Y. Wang Y. J. Mol. Catal. A: Chem. 2005; 229: 7
  • 13 Corma A. García H. Leyva A. J. Catal. 2006; 240: 87
  • 14 Iranpoor N. Firouzabadi H. Riazi A. Shakerpoor A. Appl. Organomet. Chem. 2013; 27: 451
  • 15 Karami K. Moghadam ZK. Hosseini-Kharat M. Catal. Commun. 2014; 43: 25
  • 16 Hennings DD. Iwama T. Rawal VH. Org. Lett. 1999; 1: 1205
  • 17 Xia J. Cheng M. Chen Q. Cai M. Appl. Organomet. Chem. 2015; 29: 113
  • 18 Karimi B. Vafaeezadeh M. Akhavan PF. ChemCatChem 2015; 7: 2248
  • 19 Zeng M. Zhang X. Shao L. Qi C. Zhang X.-M. J. Organomet. Chem. 2012; 704: 29
  • 20 Miyaura N. Suzuki A. Chem. Rev. 1995; 95: 2457
  • 21 Namboodiri VV. Varma RS. Green Chem. 2001; 3: 146
  • 22 Li J.-H. Liu W.-J. Xie Y.-X. J. Org. Chem. 2005; 70: 5409
  • 23 Li J.-H. Hu X.-C. Liang Y. Xie Y.-X. Tetrahedron 2006; 62: 31
  • 24 Mao J. Guo J. Fang F. Ji S.-J. Tetrahedron 2008; 64: 3905
  • 25 Liu L. Zhang Y. Wang Y. J. Org. Chem. 2005; 70: 6122
  • 26 Liu W.-J. Xie Y.-X. Liang Y. Li J.-H. Synthesis 2006; 860
  • 27 Yin L. Zhang Z.-H. Wang Y.-M. Tetrahedron 2006; 62: 9359
  • 28 Li B. Wang C. Chen G. Zhang Z. J. Environ. Sci. 2013; 25: 1083
  • 29 de Souza AL. F. Silva A. dC. Antunes OA. C. Appl. Organomet. Chem. 2009; 23: 5
  • 30 Silva A. dC. Senra JD. Aguiar LC. S. Simas AB. C. de Souza AL. F. Malta LF. B. Antunes OA. C. Tetrahedron Lett. 2010; 51: 3883
  • 31 Han W. Liu C. Jin Z.-L. Org. Lett. 2007; 9: 4005
  • 32 Han W. Liu C. Jin Z. Adv. Synth. Catal. 2008; 350: 501
  • 33 Liu C. Li X. Chem. Rec. 2016; 16: 84
  • 34 Mao J. Hua Q. Xie G. Guo J. Yao Z. Shi D. Ji S. Adv. Synth. Catal. 2009; 351: 635
  • 35 Mao J. Hua Q. Xie G. Yao Z. Shi D. Eur. J. Org. Chem. 2009; 2262
  • 36 Razler TM. Hsiao Y. Qian F. Fu R. Khan RK. Doubleday W. J. Org. Chem. 2009; 74: 1381
  • 37 García-Suárez EJ. Lara P. García AB. Ojeda M. Luque R. Philippot K. Appl. Catal., A. 2013; 468: 59
  • 38 Li F. Suo QL. Hong HL. Han LM. Adv. Mater. Res. 2012; 550–553: 639
  • 39 Xiang L. Xiaohua Z. Ming L. Appl. Organomet. Chem. 2013; 27: 615
  • 40 Blettner CG. König WA. Stenzel W. Schotten T. J. Org. Chem. 1999; 64: 3885
  • 41 Blettner CG. König WA. Rühter G. Stenzel W. Schotten T. Synlett 1999; 307
  • 42 Glegoła K. Framery E. Pietrusiewicz KM. Sinou D. Adv. Synth. Catal. 2006; 348: 1728
  • 43 Adidou O. Goux-Henry C. Safi M. Soufiaoui M. Framery E. Tetrahedron Lett. 2008; 49: 7217
  • 44 Liu N. Liu C. Yan B. Jin Z. Appl. Organomet. Chem. 2011; 25: 168
  • 45 Liu N. Liu C. Jin Z. J. Organomet. Chem. 2011; 696: 2641
  • 46 Liu N. Liu C. Jin Z. Green Chem. 2012; 14: 592
  • 47 Shi J.-C. Yu H. Jiang D. Yu M. Huang Y. Nong L. Zhang Q. Jin Z. Catal. Lett. 2014; 144: 158
  • 48 Xue J. Zhou Z. Peng J. Du F. Xie L. Xu G. Huang G. Xie Y. Transition Met. Chem. 2014; 39: 221
  • 49 Wang C. Ciganda R. Salmon L. Gregurec D. Irigoyen J. Moya S. Ruiz J. Astruc D. Angew. Chem. Int. Ed. 2016; 55: 3091
  • 50 Deraedt C. Salmon L. Ruiz J. Astruc D. Adv. Synth. Catal. 2013; 355: 2992
  • 51 Uozumi Y. Nakai Y. Org. Lett. 2002; 4: 2997
  • 52 an der Heiden M. Plenio H. Chem. Eur. J. 2004; 10: 1789
  • 53 Yang Q. Ma S. Li J. Xiao F. Xiong H. Chem. Commun. 2006; 2495
  • 54 Sin E. Yi S.-S. Lee Y.-S. J. Mol. Catal. A: Chem. 2010; 315: 99
  • 55 Sher Shah MS. A. Guin D. Manorama SV. Mater. Chem. Phys. 2010; 124: 664
  • 56 Zhang Y. Wei X. Yao Z. Chin. J. Chem. 2010; 28: 2274
  • 57 Zhang G. Zhang W. Luan Y. Han X. Ding C. Chin. J. Chem. 2015; 33: 705
  • 58 Dumas A. Peramo A. Desmaële D. Couvreur P. Chimia 2016; 70: 252
  • 59 Chinchilla R. Najera C. Chem. Rev. 2007; 107: 874
  • 60 Xia M. Wang YG. J. Chem. Res., Synop. 2002; 173
  • 61 Chen G. Xie JW. Weng J. Zhu XH. Zheng ZC. Cai JW. Wan YQ. Synth. Commun. 2011; 41: 3123
  • 62 Mao JC. Wu MY. Xie GL. Ji SJ. Adv. Synth. Catal. 2009; 351: 2101
  • 63 Firouzabadi H. Iranpoor N. Ghaderi A. Org. Biomol. Chem. 2011; 9: 865
  • 64 Firouzabadi H. Iranpoor N. Kazemi F. Gholinejad M. J. Mol. Catal. A: Chem. 2012; 357: 154
  • 65 Liu N. Liu C. Xu Q. Jin Z. Eur. J. Org. Chem. 2011; 4422
  • 66 Kidwai M. Mishra NK. Bhardwaj S. Jahan A. Kumar A. Mozumdar S. ChemCatChem 2010; 2: 1312
  • 67 Chen J. Yuan T. Hao W. Cai M. Tetrahedron Lett. 2011; 52: 3710
  • 68 Carvalho LC. R. Pires MJ. D. Fernandes E. Marques MM. B. RSC Adv. 2013; 3: 25711
  • 69 Stille JK. Angew. Chem., Int. Ed. Engl. 1986; 25: 508
  • 70 Zhou W.-J. Wang K.-H. Wang J.-X. Adv. Synth. Catal. 2009; 351: 1378
  • 71 Zhou W.-J. Wang K.-H. Wang J.-X. J. Org. Chem. 2009; 74: 5599
  • 72 Xu G. Zhang Y. Wang K. Fu Y. Du Z. J. Chem. Res. 2015; 39: 399
  • 73 Tokuyama H. Yokoshima S. Yamashita T. Fukuyama T. Tetrahedron Lett. 1998; 39: 3189
  • 74 Fang W.-J. Yakovleva T. Aldrich JV. Pept. Sci. 2011; 96: 715
  • 75 Uozumi Y. Shibatomi K. J. Am. Chem. Soc. 2001; 123: 2919
  • 76 Wang XC. Yang GJ. Quan ZJ. Ji PY. Liang JL. Ren RG. Synlett 2010; 1657
  • 77 Firouzabadi H. Iranpoor N. Gholinejad M. Adv. Synth. Catal. 2010; 352: 119
  • 78 Firouzabadi H. Iranpoor N. Gholinejad M. Samadi A. J. Mol. Catal. A: Chem. 2013; 377: 190
  • 79 Firouzabadi H. Iranpoor N. Samadi A. Tetrahedron Lett. 2014; 55: 1212
  • 80 Wang P. Lu J. Zhang ZH. J. Chem. Res. 2013; 359
  • 81 Reddy KH. V. Satish G. Ramesh K. Karnakar K. Nageswar YV. D. Chem. Lett. 2012; 41: 585
  • 82 Vaddula B. Leazer J. Varma RS. Adv. Synth. Catal. 2012; 354: 986
  • 83 Yao L. Zhou Q. Han W. Wei S. Eur. J. Org. Chem. 2012; 6856
  • 84 Yong L. Yao ML. Blevins DW. Kabalk GW. Dalton Trans. 2015; 44: 4759