Rhodium(III)-Catalyzed ortho-C–H Alkylation of 2-Arylbenzothiazoles and 2-Arylthiazoles with Potassium Alkyltrifluoroborates

Yuanyuan Ping; Zhaobin Chen; Qiuping Ding; Yiyuan Peng

doi:10.1055/s-0036-1588936

Synthesis, Table of Contents

Synthesis 2017; 49(09): 2015-2024
DOI: 10.1055/s-0036-1588936

paper

Rhodium(III)-Catalyzed ortho-C–H Alkylation of 2-Arylbenzothiazoles and 2-Arylthiazoles with Potassium Alkyltrifluoroborates

Yuanyuan Ping

Key Laboratory of Small Functional Organic Molecule, Ministry of Education and Jiangxi’s Key Laboratory of Green Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China Email: dingqiuping@jxnu.edu.cn

,

Zhaobin Chen

Key Laboratory of Small Functional Organic Molecule, Ministry of Education and Jiangxi’s Key Laboratory of Green Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China Email: dingqiuping@jxnu.edu.cn

,

Qiuping Ding*

Key Laboratory of Small Functional Organic Molecule, Ministry of Education and Jiangxi’s Key Laboratory of Green Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China Email: dingqiuping@jxnu.edu.cn

,

Yiyuan Peng

Key Laboratory of Small Functional Organic Molecule, Ministry of Education and Jiangxi’s Key Laboratory of Green Chemistry, Jiangxi Normal University, Nanchang, Jiangxi 330022, P. R. of China Email: dingqiuping@jxnu.edu.cn

› Author Affiliations

Abstract

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Abstract

A general and efficient Rh(III)-catalyzed ortho-C–H alkylation of 2-arylbenzothizazoles and 2-arylthiazoles with potassium alkyltrifluoroborates has been developed. The present method leads to the construction of a library of alkylated 2-arylbenzothiazoles and 2-arylthiazoles with yields up to 99%.

Key words

alkylation - alkyltrifluoroborates - 2-arylbenzothiazoles - 2-arylthiazoles - transition metal

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References

References

For pertinent reviews, see:

1a Schöherr H, Cernak T. Angew. Chem. Int. Ed. 2013; 52: 12256
1b Leung CS, Leung SS. F, Tirado-Rives J, Jorgensen WL. J. Med. Chem. 2012; 55: 4489
1c Barreiro EJ, Kümmerle AE, Fraga CA. M. Chem. Rev. 2011; 111: 5215

2a Vitaku E., Ilardi E. A., Njardarson J. T.; Top 200 Pharmaceutical Products by US Retail Sales in 2011; http://njardarson.lab.arizona.edu/sites/njardarson.lab.arizona.edu/files/Top%20200%20 Pharmaceutical%20Products%20by%20US%20Retail%20Sales% 20in%202011_small_0.pdf; accessed February 9, 2017.
2b For the 2008 edition, see: McGrath NA, Brichacek M, Njardarson JT. J. Chem. Educ. 2010; 87: 1348

For reviews, see:

3a Kakiuchi F, Chatani N. Adv. Synth. Catal. 2003; 345: 1077
3b Chen X, Engle KM, Wang D.-H, Yu J.-Q. Angew. Chem. Int. Ed. 2009; 48: 5094
3c Ackermann L. Chem. Commun. 2010; 46: 4866
3d Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
3e Colby DA, Tsai AS, Bergman RG, Ellman JA. Acc. Chem. Res. 2012; 45: 814
3f Pan S, Shibata T. ACS Catal. 2013; 3: 704
3g Yan G, Borah AJ, Wang L, Yang M. Adv. Synth. Catal. 2015; 357: 133

Some selected reports in recent three years:

4a Song W, Lackner S, Ackermann L. Angew. Chem. Int. Ed. 2014; 53: 2477
4b Wu X, Zhao Y, Ge H. J. Am. Chem. Soc. 2014; 136: 1789
4c Monks BM, Fruchey ER, Cook SP. Angew. Chem. Int. Ed. 2014; 53: 11065
4d Chen K, Shi BF. Angew. Chem. Int. Ed. 2014; 53: 11950
4e Zhu RY, He J, Wang XC, Yu JQ. J. Am. Chem. Soc. 2014; 136: 13194
4f Wu X, See JW. T, Xu K, Hirao H, Roger J, Hierso J, Zhou J. Angew. Chem. Int. Ed. 2014; 53: 13573
4g Zhang SY, Li Q, He G, Nack WA, Chen G. J. Am. Chem. Soc. 2015; 137: 531
4h Shen PX, Wang XC, Wang P, Zhu RY, Yu JQ. J. Am. Chem. Soc. 2015; 137: 11574
4i Li J, Warratz S, Zell D, De Sarkar S, Ishikawa EE, Ackermann L. J. Am. Chem. Soc. 2015; 137: 13894
4j Wiest JM, Pothig A, Bach T. Org. Lett. 2016; 18: 852
4k Cheng J, Deng X, Wang G, Li Y, Cheng X, Li G. Org. Lett. 2016; 18: 4538
4l Soni V, Jagtap RA, Gonnade RG, Punji B. ACS Catal. 2016; 6: 5666
4m Hu L, Liu X, Liao X. Angew. Chem. Int. Ed. 2016; 55: 9743

5 Ilies L, Ichikawa S, Asako S, Matsubara T, Nakamura E. Adv. Synth. Catal. 2015; 357: 2175

Some recent reports:

6a Lee DH, Kwon KH, Yi CS. J. Am. Chem. Soc. 2012; 134: 7325
6b Han SH, Choi M, Jeong T, Sharma S, Mishra NK, Park J, Oh JS, Kim WJ, Lee JS, Kim IS. J. Org. Chem. 2015; 80: 11092
6c Huang H, Liu J, Liu X, Xiao J, Zhong S, She X, Fu Z, Yin D. Fuel 2016; 182: 373
6d Zhou X, Yu S, Qi Z, Kong L, Li X. J. Org. Chem. 2016; 81: 4869
6e Deibl N, Kempe R. J. Am. Chem. Soc. 2016; 138: 10786

Some recent reports:

7a Yonehara F, Kido Y, Sugimoto H, Morita S, Yamaguchi M. J. Org. Chem. 2003; 68: 6752
7b Bajtos B, Yu M, Zhao H, Pagenkopf B. J. Am. Chem. Soc. 2007; 129: 9631
7c Zhang X, Wang Z, Fan X, Wang J. J. Org. Chem. 2015; 80: 10660

Some recent reports:

8a Tamura R, Yamada Y, Nakao Y, Hiyama T. Angew. Chem. Int. Ed. 2012; 51: 5679
8b Wang Z, Reinus BJ, Dong G. J. Am. Chem. Soc. 2012; 134: 13954
8c Oyamada J, Hou Z. Angew. Chem. Int. Ed. 2012; 51: 12828
8d Pan S, Ryu N, Shibata T. J. Am. Chem. Soc. 2012; 134: 17474
8e Schinkel M, Wang L, Bielefeld K, Ackermann L. Org. Lett. 2014; 16: 1876
8f Tang S, Wu X, Liao W, Liu K, Liu C, Luo S, Lei A. Org. Lett. 2014; 16: 3584
8g Shibata K, Chatani N. Org. Lett. 2014; 16: 5148
8h Hu G, Xu J, Li P. Org. Lett. 2014; 16: 6036
8i Lee PS, Yoshikai N. Org. Lett. 2015; 17: 22
8j Pollice R, Dastbaravardeh N, Marquise N, Mihovilovic MD, Schnurch M. ACS Catal. 2015; 5: 587
8k Shibata K, Yamaguchi T, Chatani N. Org. Lett. 2015; 17: 3584
8l Dang Y, Qu S, Tao Y, Deng X, Wang ZX. J. Am. Chem. Soc. 2015; 137: 6279
8m Hatano M, Ebe Y, Nishimura T, Yorimitsu H. J. Am. Chem. Soc. 2016; 138: 4010
8n Han S, Park J, Kim S, Lee SH, Sharma S, Mishra NK, Jung YH, Kim IS. Org. Lett. 2016; 18: 4666

Some recent reports:

9a Young AJ, White MC. J. Am. Chem. Soc. 2008; 130: 14090
9b Howell JM, Liu W, Young AJ, White MC. J. Am. Chem. Soc. 2014; 136: 5750
9c Bae S, Jang HL, Jung H, Joo JM. J. Org. Chem. 2015; 80: 690
9d Deng H, Li H, Wang L. Org. Lett. 2015; 17: 2450

10 Meng G, Szostak M. Org. Lett. 2016; 18: 796
11 Mai DN, Baxter RD. Org. Lett. 2016; 18: 3738
12 Pan S, Liu J, Li H, Wang Z, Guo X, Li Z. Org. Lett. 2010; 12: 1932

13a Hodgson DM, Charlton A, Paton RS, Thompson AL. J. Org. Chem. 2013; 78: 1508
13b Wang Z, Kuninobu Y, Kanai M. J. Am. Chem. Soc. 2015; 137: 6140
13c Cheng G, Li TJ, Yu JQ. J. Am. Chem. Soc. 2015; 137: 10950
13d Li DD, Niu LF, Ju ZY, Xu Z, Wu C. Eur. J. Org. Chem. 2016; 3090

14 Manna MS, Mukherjee S. J. Am. Chem. Soc. 2015; 137: 130
15 Chen X, Li J.-J, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 78
16 Kubo T, Chatani N. Org. Lett. 2016; 18: 1698

17a Uraguchi D, Sorimachi K, Terada M. J. Am. Chem. Soc. 2005; 127: 9360
17b Choi M, Park J, Mishra NK, Lee S.-Y, Kim JH, Jeong KM, Lee J, Jung YH, Kim IS. Tetrahedron Lett. 2015; 56: 4678

18a Chen X, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 12634
18b Castro S, Fernández JJ, Fañanás FJ, Vicente R, Rodríguez F. Chem. Eur. J. 2016; 22: 9068
18c Zhang Y, Jiang H, Chen D, Zhang Y. Org. Biomol. Chem. 2016; 14: 4585
18d Sarkar D, Gevorgyan V. Chem. Eur. J. 2016; 22: 11201
18e Molander GA, Colombel V, Braz VA. Org. Lett. 2011; 13: 1852
18f Thuy-Boun PS, Villa G, Dang D, Richardson P, Su S, Yu J.-Q. J. Am. Chem. Soc. 2013; 135: 17508
18g Wang H, Yu S, Qi Z, Li X. Org. Lett. 2015; 17: 2812
18h Peng P, Wang J, Jiang H, Liu H. Org. Lett. 2016; 18: 5376

19a Benavides J, Camelin JC, Mitrani N, Flamand F, Uzan A, Legrand JJ, Guérémy C, Le Fur G. Neuropharmacology 1985; 24: 1085
19b Malgouris C, Bardot F, Daniel M, Pellis J, Rataud A, Uzan A, Blanchard JC, Laduron PM. J. Neurosci. 1989; 9: 3720
19c Mortimer CG, Wells G, Crochard JP, Stone EL, Bradshaw TD, Stevens MF. G, Westwell AD. J. Med. Chem. 2006; 49: 179
19d Aiello S, Wells G, Stone EL, Kadri H, Bazzi R, Bell DR, Stevens MF. G, Matthews CS, Bradshaw TD, Westwell AD. J. Med. Chem. 2008; 51: 5135

20a Katkova MA, Balashova TV, Ilichev VA, Konev AN, Isachenkov NA, Fukin GK, Ketkov SU, Bochkarev MN. Inorg. Chem. 2010; 49: 5094
20b Wang R, Liu D, Ren H, Zhang T, Wang X, Li J. J. Mater. Chem. 2011; 21: 15494
20c Santra M, Roy B, Ahn KH. Org. Lett. 2011; 13: 3422
20d Woo H, Cho S, Han Y, Chae W.-S, Ahn D.-R, You Y, Nam W. J. Am. Chem. Soc. 2013; 135: 4771
20e Yuan Y.-J, Yu Z.-T, Gao H.-L, Zou Z.-G, Zheng C, Huang W. Chem. Eur. J. 2013; 19: 6340

21a Ding Q, Ji H, Wang D, Lin Y, Yu W, Peng Y. J. Organomet. Chem. 2012; 711: 62
21b Ding Q, Ji H, Nie Z, Yang Q, Peng Y. J. Organomet. Chem. 2013; 739: 33
21c Ding Q, Ye C, Pu S, Cao B. Tetrahedron 2014; 70: 409
21d Ding Q, Zhou X, Pu S, Cao B. Tetrahedron 2015; 71: 2376
21e Zhou X, Luo P, Long L, Ouyang M, Sang X, Ding Q. Tetrahedron 2014; 70: 6742
21f Ding Q, Ji H, Ye C, Wang J, Wang J, Zhou L, Peng Y. Tetrahedron 2013; 69: 8661
21g Wang J, Nie Z, Li Y, Tan S, Jiang J, Jiang P, Ding Q. J. Chem. Res. 2013; 37: 263
21h Luo P, Ding Q, Ping Y, Hu J. Org. Biomol. Chem. 2016; 14: 2924
21i Ping Y, Ding Q, Chen Z, Peng Y. J. Organomet. Chem. 2016; 815–816: 59

22a Hashimoto Y, Ortloff T, Hirano K, Satoh T, Bolm C, Miura M. Chem. Lett. 2012; 41: 151
22b Banerjee A, Santra SK, Guin S, Rout SK, Patel BK. Eur. J. Org. Chem. 2013; 7: 1367
22c Zheng Y, Song WB, Zhang SW, Xuan LJ. Tetrahedron 2015; 71: 1574
22d Banerjee A, Bera A, Guin S, Rout SK, Patel BK. Tetrahedron 2013; 69: 2175
22e Seth K, Nautiyal M, Purohit P, Parikh N, Chakraborti AK. Chem. Commun. 2015; 51: 191
22f Qiao H.-J, Yang F, Wang S.-W, Leng Y.-T, Wu Y.-J. Tetrahedron 2015; 71: 9258

23a Hartmann CE, Nolan SP, Cazin CS. Organometallics 2009; 28: 2915
23b Hachiya H, Hirano K, Satoh T, Miura M. Org. Lett. 2009; 11: 1737
23c Julliard M, Siv C, Vernin G, Jacques M. Helv. Chim. Acta 1978; 61: 2941
23d Tani S, Uehara TN, Yamaguchi J, Itami K. Chem. Sci. 2014; 5: 123

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