Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids

Ya-Nan Cao; Xin-Chuan Tian; Xing-Xiu Chen; Yun-Xin Yao; Feng Gao; Xian-Li Zhou

doi:10.1055/s-0036-1588361

Synlett, Table of Contents

Synlett 2017; 28(05): 601-606
DOI: 10.1055/s-0036-1588361

letter

Rapid Ligand-Free Base-Accelerated Copper-Catalyzed Homocoupling Reaction of Arylboronic Acids

Ya-Nan Cao

^aSchool of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, P. R. of China

^bDepartment of Chinese Traditional Herbal, Agronomy College, Sichuan Agriculture University, Chengdu 611130, P. R. of China Email: gaofeng@sicau.edu.cn Email: xxbiochem@163.com

,

Xin-Chuan Tian

^bDepartment of Chinese Traditional Herbal, Agronomy College, Sichuan Agriculture University, Chengdu 611130, P. R. of China Email: gaofeng@sicau.edu.cn Email: xxbiochem@163.com

,

Xing-Xiu Chen

^bDepartment of Chinese Traditional Herbal, Agronomy College, Sichuan Agriculture University, Chengdu 611130, P. R. of China Email: gaofeng@sicau.edu.cn Email: xxbiochem@163.com

,

Yun-Xin Yao

^bDepartment of Chinese Traditional Herbal, Agronomy College, Sichuan Agriculture University, Chengdu 611130, P. R. of China Email: gaofeng@sicau.edu.cn Email: xxbiochem@163.com

,

Feng Gao*

^aSchool of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, P. R. of China

^bDepartment of Chinese Traditional Herbal, Agronomy College, Sichuan Agriculture University, Chengdu 611130, P. R. of China Email: gaofeng@sicau.edu.cn Email: xxbiochem@163.com

,

Xian-Li Zhou*

^aSchool of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031, P. R. of China

› Author Affiliations

Abstract

All articles of this category

Abstract

A rapid, ligand-free, base-accelerated, copper-catalyzed homocoupling reaction of (het)arylboronic acids is presented. A CuCl₂·2H₂O/Na₂CO₃-based catalyst enabled the formation of bi(het)aryl compounds by a homocoupling process in moderate to excellent yields (72–97%) within 15 minutes. A mechanism for the copper-catalyzed base-accelerated reaction is proposed.

Key words

homocoupling - arylboronic acids - copper catalysis - biaryls

Full Text

References

References and Notes
1 Kozlowski MC, Morgan BJ, Linton EC. Chem. Soc. Rev. 2009; 38: 3193

2a Ezaki M, Iwami M, Yamashita M, Hashimoto S, Komori T, Umehara K, Mine Y, Kohsaka M, Aoiki H, Imanaka H. J. Antibiot. 1985; 38: 1453
2b Uchida I, Ezaki M, Shigematsu N, Hashimoto M. J. Org. Chem. 1985; 50: 1341
2c Chang CC, Morton GO, James JC, Siegel MM, Kuck NA, Testa RT, Borders DB. J. Antibiot. 1991; 44: 674
2d Lépine R, Zhu JP. Org. Lett. 2005; 7: 2981

3a Nelson RA, Pope JA. Jr, Luedemann GM, McDaniel LE, Schaffner CP. J. Antibiot. 1986; 39: 335
3b Ling D, Shield LS, Rinehart KL. Jr. J. Antibiot. 1986; 39: 345
3c Li Z, Gao Y, Tang Y, Dai M, Wang G, Wang Z, Yang Z. Org. Lett. 2008; 10: 3017

4a Kraft A, Grimsdale AC, Holmes AB. Angew. Chem. Int. Ed. 1998; 37: 402
4b McFarland SA, Finney NS. J. Am. Chem. Soc. 2001; 123: 1260
4c Long Y.-T, Rong H.-T, Buck M, Grunze M. J. Electroanal. Chem. 2002; 524: 62
4d Casalbore-Miceli G, Degli Esposti A, Fattori V, Marconi G, Sabatini C. Phys. Chem. Chem. Phys. 2004; 6: 3092

5a Hassan J, Sévignon M, Gozzi C, Schulz E, Lemaire M. Chem. Rev. 2002; 102: 1359
5b Chen Y, Yekta S, Yudin AK. Chem. Rev. 2003; 103: 3155
5c Khanbabaee K, Basceken S, Flörke U. Tetrahedron: Asymmetry 2006; 17: 2804
5d Corbet J.-P, Mignani G. Chem. Rev. 2006; 106: 2651

6a Deng JZ, Paone DV, Ginnetti AT, Kurihara H, Dreher SD, Weissman SA, Stauffer SR, Burgey CS. Org. Lett. 2008; 11: 345
6b Jin M.-J, Lee D.-H. Angew. Chem. Int. Ed. 2010; 49: 1119
6c Yuan B, Pan Y, Li Y, Yin B, Jiang H. Angew. Chem. 2010; 122: 4148
6d Schmidt B, Riemer M. J. Org. Chem. 2014; 79: 4104
6e Gurung SK, Thapa S, Kafle A, Dickie DA, Giri R. Org. Lett. 2014; 16: 1264

7a Roling PV, Rausch MD. J. Org. Chem. 1972; 37: 729
7b Nettekoven U, Widhalm M, Kamer PC. J, van Leeuwen PW. N. M, Mereiter K, Lutz M, Spek AL. Organometallics 2000; 19: 2299
7c Karimi B, Esfahani FK. Chem. Commun. 2011; 47: 10452
7d Wang W, Shi X, Wang S, Van Hove MA, Lin N. J. Am. Chem. Soc. 2011; 133: 13264
7e Kamal A, Srinivasulu V, Seshadri BN, Markandeya N, Alarifi A, Shankaraiah N. Green Chem. 2012; 14: 2513
7f Lewis EA, Murphy CJ, Liriano ML, Sykes EC. H. Chem. Commun. 2014; 50: 1006
7g Nasrollahzadeh M, Sajadi SM, Khalaj M. RSC Adv. 2014; 4: 47313
7h Zhang C, Sun Q, Chen H, Tan Q, Xu W. Chem. Commun. 2015; 51: 495

8 Suzuki A. Angew. Chem. Int. Ed. 2011; 50: 6722

9a Parrish JP, Jung YC, Floyd RJ, Jung KW. Tetrahedron Lett. 2002; 43: 7899
9b Xu Z, Mao J, Zhang Y. Catal. Commun. 2008; 9: 97
9c Mitsudo K, Shiraga T, Kagen D, Shi D, Becker JY, Tanaka H. Tetrahedron 2009; 65: 8384
9d Mu B, Li T, Fu Z, Wu Y. Catal. Commun. 2009; 10: 1497
9e Prastaro A, Ceci P, Chiancone E, Boffi A, Fabrizi G, Cacchi S. Tetrahedron Lett. 2010; 51: 2550
9f Santos-Filho EF, Sousa JC, Bezerra NM. M, Menezes PH, Oliveira RA. Tetrahedron Lett. 2011; 52: 5288
9g Dwivedi S, Bardhan S, Ghosh P, Das S. RSC Adv. 2014; 4: 41045
9h Kapdi AR, Dhangar G, Serrano JL, De Haro JA, Lozanod P, Fairlamb IJ. S. RSC Adv. 2014; 4: 55305
9i Wu N, Li X, Xu X, Wang Y, Xu Y, Chen X. Lett. Org. Chem. 2010; 7: 11
9j Mitsudo K, Shiraga T, Tanaka H. Tetrahedron Lett. 2008; 49: 6593
9k Xia JH, Cheng MZ, Chen QR, Cai MZ. Appl. Organomet. Chem. 2015; 29: 113
9l Li M, González-Esguevillas M, Berritt S, Yang X, Bellomo A, Walsh PJ. Angew. Chem. Int. Ed. 2016; 55: 2825

10a Baig RB. N, Varma RS. Green Chem. 2013; 15: 398
10b Carrettin S, Guzman J, Corma A. Angew. Chem. Int. Ed. 2005; 44: 2242
10c Zheng J, Lin S, Zhu X, Jiang B, Yang Z, Pan Z. Chem. Commun. 2012; 48: 6235
10d Dhital RN, Kamonsatikul C, Somsook E, Sato Y, Sakurai H. Chem. Commun. 2013; 49: 2542
10e Sk MP, Jana CK, Chattopadhyay A. Chem. Commun. 2013; 49: 8235
10f Wang L, Wang H, Zhang W, Zhang J, Lewis JP, Meng X, Xiao F.-S. J. Catal. 2013; 298: 186
10g Falck JR, Mohapatra S, Bondlela M, Venkataraman SK. Tetrahedron Lett. 2002; 43: 8149
10h Vogler T, Studer A. Adv. Synth. Catal. 2008; 350: 1963

11a Kaboudin B, Mostafalu R, Yokomatsu T. Green Chem. 2013; 15: 2266
11b Dar BA, Singh S, Pandey N, Singh AP, Sharma P, Lazar A, Sharma M, Vishwakarma RA, Singh B. Appl. Catal., A 2014; 470: 232
11c Puthiaraj P, Suresh P, Pitchumani K. Green Chem. 2014; 16: 2865
11d Mulla SA. R, Chavan SS, Pathan MY, Inamdar SM, Shaikh TM. Y. RSC Adv. 2015; 5: 24675
11e Hussain N, Gogoi P, Azhaganand VK, Shelke MV, Das MR. Catal. Sci. Technol. 2015; 5: 1251
11f Demir AS, Reis Ö, Emrullahoglu M. J. Org. Chem. 2003; 68: 10130
11g Kirai N, Yamamoto Y. Eur. J. Org. Chem. 2009; 1864
11h Kaboudin B, Haruki T, Yokomatsu T. Synthesis 2011; 91
11i Cheng GJ, Luo MM. Eur. J. Org. Chem. 2011; 2519
11j Raul PK, Mahanta A, Bora U, Thakur AJ, Veer V. Tetrahedron Lett. 2015; 56: 7069

12 Fihri A, Bouhrara M, Nekoueishahraki B, Basset J.-M, Polshettiwar V. Chem. Soc. Rev. 2011; 40: 5181

13a Tian X.-C, Huang X, Wang D, Gao F. Chem. Pharm. Bull. 2014; 62: 824
13b Gao F, Kim B.-S, Walsh PJ. Chem. Commun. 2014; 50: 10661
13c Gao F, Tian X.-C, Qu X.-X, Wang D, Pu D. Synthesis 2015; 47: 65

14a Gao F, Wang D, Huang X. Fitoterapia 2013; 90: 79
14b Chen X.-X, Gao F, Wang Q, Huang X, Wang D. Fitoterapia 2014; 92: 111
14c Wen G, Qu X.-X, Wang D, Chen X.-X, Tian X.-C, Gao F, Zhou X.-L. Fitoterapia 2016; 110: 26

15a van der Bol JM, Visser TJ, Loos WJ, de Jong FA, Wiemer EA. C, van Aken MO, Planting AS, Schellens JH, Verweij J, Mathijssen RH. J. Cancer Chemother. Pharmacol. 2011; 67: 231
15b Maio M, Grob JJ, Aamdal S, Bondarenko I, Robert C, Thomas L, Garbe C, Chiarion-Sileni V, Testori A, Chen TT, Tschaika M, Wolchok JD. J. Clin. Oncol. 2015; 33: 1191
15c Amatu A, Sartore-Bianchi A, Moutinho C, Belotti A, Bencardino K, Chirico G, Cassingena A, Rusconi F, Esposito A, Nichelatti M, Esteller M, Siena S. Clin. Cancer Res. 2013; 19: 2265

16a Owen LA, Uehara H, Cahoon J, Huang W, Simonis J, Ambati BK. PLoS One 2012; 7: e33576
16b Yun CH, Boggon TJ, Li YQ, Woo MS, Greulich H, Meyerson M, Eck MJ. Cancer Cell 2007; 11: 217
16c Morales G, Picazo JJ, Baos E, Candel FJ, Arribi A, Peláez B, Andrade R, de la Torre MÁ, Fereres J, Sánchez-García M. Clin. Infect. Dis. 2010; 50: 821

17a Markó IE, Giles PR, Tsukazaki M, Brown SM, Christopher JU. Science 1996; 274: 2044
17b Markó IE, Tsukazaki M, Giles PR, Brown SM, Christopher JU. Angew. Chem. Int. Ed. 1997; 36: 2208

18 Rao H, Fu H. Synlett 2011; 745 ; and references therein
19 Carrow BP, Hartwig JF. J. Am. Chem. Soc. 2011; 133: 2116
20 Miyaura N. J. Organomet. Chem. 2002; 653: 54
21 Ding S, Xu L, Li P. ACS Catal. 2016; 6: 1329
22 Bi(het)aryls 2a–t; General Procedure A vial was charged with the appropriate (het)arylboronic acid (0.3 mmol), CuCl₂·2H₂O (2.5 mg, 5 mol%), Na₂CO₃ (10 mol%), and MeOH (1 mL), and the mixture was stirred at 25 °C in the air for 5–15 min while the reaction was monitored by TLC. The reaction was then quenched with two drops of H₂O. The mixture was then diluted with EtOAc (2 mL) and filtered through a pad of MgSO₄ and silica. The pad was rinsed with additional EtOAc, and the solution was concentrated in vacuum. The crude material was purified by flash chromatography (silica gel). 4,4′-Di-tert-butylbiphenyl (2a) Prepared by following the general procedure with (4-tert-butylphenyl)boronic acid (53.4 mg, 0.3 mmol) for 15 min at r.t. Purification by flash chromatography (silica gel, PE) gave a white solid; yield: 37.9 mg (95%); mp 126–127 °C. ¹H NMR (400 MHz, CDCl₃): δ = 7.57 (d, J = 8.4 Hz, 4 H), 7.49 (d, J = 8.4 Hz, 4 H), 1.40 (s, 18 H). ¹³C{¹H} NMR (100 MHz, CDCl₃): δ = 149.9, 138.2, 126.6, 125.6, 34.5, 31.4.

Supplementary Material

Supporting Information