Copper-Catalyzed Cross-Coupling of Aryl- and Heteroaryltriethoxysilanes with Aryl and Heteroaryl Iodides and Bromides

Santosh K. Gurung; Surendra Thapa; Bijay Shrestha; Ramesh Giri

doi:10.1055/s-0033-1339108

Synthesis, Table of Contents

Synthesis 2014; 46(14): 1933-1937
DOI: 10.1055/s-0033-1339108

special topic

Copper-Catalyzed Cross-Coupling of Aryl- and Heteroaryltriethoxysilanes with Aryl and Heteroaryl Iodides and Bromides

Santosh K. Gurung

Department of Chemistry & Chemical Biology, The University of New Mexico, Albuquerque, NM 87131, USA Fax: +1(505)2772609 Email: rgiri@unm.edu

,

Surendra Thapa

Department of Chemistry & Chemical Biology, The University of New Mexico, Albuquerque, NM 87131, USA Fax: +1(505)2772609 Email: rgiri@unm.edu

,

Bijay Shrestha

Department of Chemistry & Chemical Biology, The University of New Mexico, Albuquerque, NM 87131, USA Fax: +1(505)2772609 Email: rgiri@unm.edu

,

Ramesh Giri*

Department of Chemistry & Chemical Biology, The University of New Mexico, Albuquerque, NM 87131, USA Fax: +1(505)2772609 Email: rgiri@unm.edu

› Author Affiliations

Abstract

All articles of this category

Abstract

Copper(I)-catalyzed coupling of aryl- and heteroaryltriethoxysilanes with aryl and heteroaryl iodides is described. The transformation also proceeds with activated aryl bromides, but in this case it requires a stoichiometric amount of the catalyst for best product yields. The current reaction requires a P,N-based bidentate ligand for aryl–aryl coupling while it proceeds without external ligands for aryl–heteroaryl coupling to afford good product yields. The reaction protocol can also be applied to achieve biarylation of diiodoarenes in reasonable yields.

Key words

aryltriethoxysilane - biarylation - catalytic cycle - cross-coupling - P,N-ligand

Full Text

References

References

1a Nakao Y, Hiyama T. Chem. Soc. Rev. 2011; 40: 4893
1b Chang W.-TT, Smith RC, Regens CS, Bailey AD, Werner NS, Denmark SE. Org. React. 2011; 75: 213

2a Sore HF, Galloway WR. J. D, Spring DR. Chem. Soc. Rev. 2012; 41: 1845
2b Hiyama T. J. Organomet. Chem. 2002; 653: 58
2c Handy CJ, Manoso AS, McElroy WT, Seganish WM, DeShong P. Tetrahedron 2005; 61: 12201
2d Shukla KH, DeShong P. Heterocycles 2012; 86: 1055

3a Denmark SE, Liu JH. C. Angew. Chem. Int. Ed. 2010; 49: 2978
3b Denmark SE, Sweis RF. J. Am. Chem. Soc. 2001; 123: 6439

For selected examples of nickel-catalyzed Suzuki–Miyaura coupling, see:

4a Zhou J, Fu GC. J. Am. Chem. Soc. 2004; 126: 1340
4b González-Bobes F, Fu GC. J. Am. Chem. Soc. 2006; 128: 5360
4c Saito B, Fu GC. J. Am. Chem. Soc. 2007; 129: 9602
4d Tobisu M, Shimasaki T, Chatani N. Angew. Chem. Int. Ed. 2008; 47: 4866
4e Quasdorf KW, Tian X, Garg NK. J. Am. Chem. Soc. 2008; 130: 14422
4f Guan B.-T, Wang Y, Li B.-J, Yu D.-G, Shi Z.-J. J. Am. Chem. Soc. 2008; 130: 14468
4g Antoft-Finch A, Blackburn T, Snieckus V. J. Am. Chem. Soc. 2009; 131: 17750
4h Quasdorf KW, Riener M, Petrova KV, Garg NK. J. Am. Chem. Soc. 2009; 131: 17748
4i Quasdorf KW, Antoft-Finch A, Liu P, Silberstein AL, Komaromi A, Blackburn T, Ramgren SD, Houk KN, Snieckus V, Garg NK. J. Am. Chem. Soc. 2011; 133: 6352
4j Lu Z, Wilsily A, Fu GC. J. Am. Chem. Soc. 2011; 133: 8154
4k Tobisu M, Xu T, Shimasaki T, Chatani N. J. Am. Chem. Soc. 2011; 133: 19505
4l Ge S, Hartwig JF. Angew. Chem. Int. Ed. 2012; 51: 12837

For Fe-catalyzed Suzuki–Miyaura coupling, see:

4m Guo Y, Young DJ, Hor TS. A. Tetrahedron Lett. 2008; 49: 5620
4n Hatakeyama T, Hashimoto T, Kondo Y, Fujiwara Y, Seike H, Takaya H, Tamada Y, Ono T, Nakamura M. J. Am. Chem. Soc. 2010; 132: 10674

5a Powell DA, Fu GC. J. Am. Chem. Soc. 2004; 126: 7788
5b Strotman NA, Sommer S, Fu GC. Angew. Chem. Int. Ed. 2007; 46: 3556
5c Dai X, Strotman NA, Fu GC. J. Am. Chem. Soc. 2008; 130: 3302

6a Okuro K, Furuune M, Enna M, Miura M, Nomura M. J. Org. Chem. 1993; 58: 4716
6b Ma D, Cai Q. Acc. Chem. Res. 2008; 41: 1450
6c Gujadhur RK, Bates CG, Venkataraman D. Org. Lett. 2001; 3: 4315
6d Li J.-H, Li J.-L, Wang D.-P, Pi S.-F, Xie Y.-X, Zhang M.-B, Hu X.-C. J. Org. Chem. 2007; 72: 2053
6e Monnier F, Turtaut FO, Duroure L, Taillefer M. Org. Lett. 2008; 10: 3203
6f Zou L.-H, Johansson AJ, Zuidema E, Bolm C. Chem. Eur. J. 2013; 19: 8144

7a Takeda T, Matsunaga KI, Kabasawa Y, Fujiwara T. Chem. Lett. 1995; 771
7b Falck JR, Bhatt RK, Ye J. J. Am. Chem. Soc. 1995; 117: 5973
7c Allred GD, Liebeskind LS. J. Am. Chem. Soc. 1996; 118: 2748
7d Kang S.-K, Kim J.-S, Choi S.-C. J. Org. Chem. 1997; 62: 4208

8a Thathagar MB, Beckers J, Rothenberg G. J. Am. Chem. Soc. 2002; 124: 11858
8b Thathagar MB, Beckers J, Rothenberg G. Adv. Synth. Catal. 2003; 345: 979
8c Li J.-H, Wang D.-P. Eur. J. Org. Chem. 2006; 2063
8d Li J.-H, Li J.-L, Xie Y.-X. Synthesis 2007; 984
8e Mao J, Guo J, Fang F, Ji S.-J. Tetrahedron 2008; 64: 3905
8f Ye Y.-M, Wang B.-B, Ma D, Shao L.-X, Lu J.-M. Catal. Lett. 2010; 139: 141
8g Yang C.-T, Zhang Z.-Q, Liu Y.-C, Liu L. Angew. Chem. Int. Ed. 2011; 50: 3904
8h Wang S, Wang M, Wang L, Wang B, Li P, Yang J. Tetrahedron 2011; 67: 4800
8i Gurung SK, Thapa S, Kafle A, Dickie DA, Giri R. Org. Lett. 2014; 16: 1264

9 Liwosz TW, Chemler SR. Org. Lett. 2013; 15: 3034

Effects of copper salts on reactions involving organosilicon reagents, see:

10a Denmark SE, Baird JD. Org. Lett. 2004; 6: 3649
10b Hanamoto T, Kobayashi T, Kondo M. Synlett 2001; 0281
10c Nakao Y, Imanaka H, Sahoo AK, Yada A, Hiyama T. J. Am. Chem. Soc. 2005; 127: 6952
10d Nakao Y, Takeda M, Matsumoto T, Hiyama T. Angew. Chem. Int. Ed. 2010; 49: 4447

For effects of copper salts on palladium-catalyzed Suzuki–Miyaura coupling, see:

10e Liu XX, Deng MZ. Chem. Commun. 2002; 622
10f Deng JZ, Paone DV, Ginnetti AT, Kurihara H, Dreher SD, Weissman SA, Stauffer SR, Burgey CS. Org. Lett. 2009; 11: 345

For effects of copper salts on nickel-catalyzed Suzuki–Miyaura coupling, see:

10g Lipshutz BH, Nihan DM, Vinogradova E, Taft BR, Bogkovic ZV. Org. Lett. 2008; 10: 4279

11 Ito H, Sensui H.-o, Arimoto K, Miura K, Hosomi A. Chem. Lett. 1997; 639

For homocouplings of vinyl-, alkynyl-, and arylsilicon reagents with stoichiometric amounts of copper salts, see:

12a Nishihara Y, Ikegashira K, Toriyama F, Mori A, Hiyama T. Bull. Chem. Soc. Jpn. 2000; 73: 985
12b Louërat F, Gros PC. Tetrahedron Lett. 2010; 51: 3558
12c Itami K, Ushiogi Y, Nokami T, Ohashi Y, Yoshida J.-i. Org. Lett. 2004; 6: 3695
12d Ikegashira K, Nishihara Y, Hirabayashi K, Mori A, Hiyama T. Chem. Commun. 1997; 1039

13a Herron JR, Ball ZT. J. Am. Chem. Soc. 2008; 130: 16486
13b Herron JR, Russo V, Valente EJ, Ball ZT. Chem. Eur. J. 2009; 15: 8713
13c Russo V, Herron JR, Ball ZT. Org. Lett. 2009; 12: 220

14 Lee KS, Hoveyda AH. J. Org. Chem. 2009; 74: 4455

15a Franz AK, Woerpel KA. J. Am. Chem. Soc. 1999; 121: 949
15b Taguchi H, Ghoroku K, Tadaki M, Tsubouchi A, Takeda T. J. Org. Chem. 2002; 67: 8450
15c Taguchi H, Ghoroku K, Tadaki M, Tsubouchi A, Takeda T. Org. Lett. 2001; 3: 3811
15d Tomita D, Wada R, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2005; 127: 4138
15e Yamasaki S, Fujii K, Wada R, Kanai M, Shibasaki M. J. Am. Chem. Soc. 2002; 124: 6536
15f Nguyen MH, Smith AB. Org. Lett. 2013; 15: 4872
15g Tsubouchi A, Muramatsu D, Takeda T. Angew. Chem. Int. Ed. 2013; 52: 12719

16a Zarotti P, Knöpfel TF, Aschwanden P, Carreira EM. ACS Catal. 2012; 2: 1232
16b Knöpfel TF, Zarotti P, Ichikawa T, Carreira EM. J. Am. Chem. Soc. 2005; 127: 9682
16c Knöpfel TF, Carreira EM. J. Am. Chem. Soc. 2003; 125: 6054

17 Gurung SK, Thapa S, Vangala AS, Giri R. Org. Lett. 2013; 15: 5378

For a similar catalytic cycle in Ullmann amination, see:

18a Strieter ER, Bhayana B, Buchwald SL. J. Am. Chem. Soc. 2009; 131: 78
18b Strieter ER, Blackmond DG, Buchwald SL. J. Am. Chem. Soc. 2005; 127: 4120
18c Giri R, Hartwig JF. J. Am. Chem. Soc. 2010; 132: 15860
18d Tye JW, Weng Z, Johns AM, Incarvito CD, Hartwig JF. J. Am. Chem. Soc. 2008; 130: 9971

19 Becht JM, Ngouela S, Wagner A, Mioskowski C. Tetrahedron 2004; 60: 6853
20 Bai L, Wang JX. Adv. Synth. Catal. 2008; 350: 315
21 Estrada LA, Montes VA, Zyryanov G, Anzenbacher P. J. Phys. Chem. B 2007; 111: 6983