Iron-Catalyzed Remote C–H Alkylation of 8-Amidoquinolines with Cycloalkanes

Wengang Xu; Mingbo Wu; Naohiko Yoshikai

doi:10.1055/a-1337-5416

Synthesis, Table of Contents

Synthesis 2021; 53(17): 3144-3150
DOI: 10.1055/a-1337-5416

special topic

Bond Activation – in Honor of Prof. Shinji Murai

Iron-Catalyzed Remote C–H Alkylation of 8-Amidoquinolines with Cycloalkanes

Authors

Wengang Xu

^aCollege of New Energy, Institute of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), Qingdao 266580, P. R. of China
Mingbo Wu∗

^aCollege of New Energy, Institute of New Energy, State Key Laboratory of Heavy Oil Processing, China University of Petroleum (East China), Qingdao 266580, P. R. of China
Naohiko Yoshikai ∗

^bDivision of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore

Abstract

All articles of this category

Abstract

An iron-catalyzed, peroxide-mediated cross-dehydrogenative coupling between 8-amidoquinolines and cycloalkanes has been developed for the site-selective alkylation of the quinoline nucleus at the C5 position. The reaction tolerates various substituted N-(quinolin-8-yl)benzamides and N-(quinolin-8-yl)alkylamides, affording the corresponding C5-alkylation products in good yields. On the basis of control experiments, a reaction mechanism involving the addition of an alkyl radical to an iron-chelated intermediate is proposed.

Key words

C–H functionalization - iron catalysis - quinolines - alkylation - radical reaction

Full Text

References

References

1a Michael JP. Nat. Prod. Rep. 2008; 25: 166
1b Solomon VR, Lee H. Curr. Med. Chem. 2011; 18: 1488
1c Colomb J, Becker G, Fieux S, Zimmer L, Billard T. J. Med. Chem. 2014; 57: 3884

2a Iwai T, Sawamura M. ACS Catal. 2015; 5: 5031
2b Khan B, Dutta HS, Koley D. Asian J. Org. Chem. 2018; 7: 1270
2c Xu Z, Yang X, Yin S.-F, Qiu R. Top. Curr. Chem. 2020; 378: 42

3 Daugulis O, Roane J, Tran LD. Acc. Chem. Res. 2015; 48: 1053
4 Suess AM, Ertem MZ, Cramer CJ, Stahl SS. J. Am. Chem. Soc. 2013; 135: 9797

Selected examples:

5a Guo H, Chen M, Jiang P, Chen J, Pan L, Wang M, Xie C, Zhang Y. Tetrahedron 2015; 71: 70
5b Zhang S, Ullah A, Yamamoto Y, Almansour AI, Arumugam N, Kumar RS, Bao M. ChemistrySelect 2017; 2: 3414
5c Ding J, Zhang Y, Li J. Org. Chem. Front. 2017; 4: 1528
5d Qiao H, Sun S, Yang F, Zhu Y, Kang J, Wu Y, Wu Y. Adv. Synth. Catal. 2017; 359: 1976
5e Du Y, Liu Y, Wan J.-P. J. Org. Chem. 2018; 83: 3403
5f Motati DR, Uredi D, Watkins EB. Chem. Sci. 2018; 9: 1782
5g Mariappan A, Das KM, Jeganmohan M. Org. Biomol. Chem. 2018; 16: 3419

6a Shen C, Yang M, Xu J, Chen C, Zheng K, Shen J, Zhang P. RSC Adv. 2017; 7: 49436
6b Vinayak B, Navyasree P, Chandrasekharam M. Org. Biomol. Chem. 2017; 15: 9200
6c Xia C, Wang K, Xu J, Shen C, Sun D, Li H, Wang G, Zhang P. Org. Biomol. Chem. 2017; 15: 531

Selected examples:

7a Liang H.-W, Jiang K, Ding W, Yuang Y, Shuai L, Chen Y.-C, Wei Y. Chem. Commun. 2015; 51: 16928
7b Zhu L, Qiu R, Cao X, Xiao S, Xu X, Au C.-T, Yin S.-F. Org. Lett. 2015; 17: 5528
7c Qiao H, Sun S, Yang F, Zhu Y, Zhu W, Dong Y, Wu Y, Kong X, Jiang L, Wu Y. Org. Lett. 2015; 17: 6086
7d Wang K, Wang G, Duan G, Xia C. RSC Adv. 2017; 7: 51313
7e Sahoo H, Mandal A, Selvakumar J, Baidya M. Eur. J. Org. Chem. 2016; 4321
7f Wei J, Jiang J, Xiao X, Lin D, Deng Y, Ke Z, Jiang H, Zeng W. J. Org. Chem. 2016; 81: 946
7g Chen G, Zhang X, Zeng Z, Peng W, Liang Q, Liu J. ChemistrySelect 2017; 2: 1979
7h Bai P, Sun S, Li Z, Qiao H, Su X, Yang F, Wu Y, Wu Y. J. Org. Chem. 2017; 82: 12119
7i Xia H, An Y, Zeng X, Wu J. Org. Chem. Front. 2018; 5: 366
7j Liu X, Zhang H, Yang F, Wang B. Org. Biomol. Chem. 2019; 17: 7564
7k Kumar V, Banert K, Ray D, Saha B. Org. Biomol. Chem. 2019; 17: 10245

Selected examples:

8a Dou Y, Xie Z, Sun Z, Fang H, Shen C, Zhang P, Zhu Q. ChemCatChem 2016; 8: 3570
8b Whiteoak CJ, Planas O, Company A, Ribas X. Adv. Synth. Catal. 2016; 358: 1679
8c Zhu X, Qiao L, Ye P, Ying B, Xu J, Shen C, Zhang P. RSC Adv. 2016; 6: 89979
8d Sahoo H, Reddy MK, Ramakrishna I, Baidya M. Chem. Eur. J. 2016; 22: 1592
8e He Y, Zhao N, Qiu L, Zhang X, Fan X. Org. Lett. 2016; 18: 6054
8f Yin Y, Xie J, Huang F.-Q, Qi L.-W, Zhang B. Adv. Synth. Catal. 2017; 359: 1037
8g Xia H, An Y, Zeng X, Wu J. Chem. Commun. 2017; 53: 12548
8h Yi H, Chen H, Bian C, Tang Z, Singh AK, Qi X, Yur X, Lan Y, Lee J.-F, Lei A. Chem. Commun. 2017; 53: 6736
8i Khan B, Khan AA, Bora D, Verma D, Koley D. ChemistrySelect 2017; 2: 260

Selected examples:

9a Chen H, Li P, Wang M, Wang L. Org. Lett. 2016; 18: 4794
9b Kuninobu Y, Nishi M, Kanai M. Org. Biomol. Chem. 2016; 14: 8092
9c Jin L.-K, Lu G.-P, Cai C. Org. Chem. Front. 2016; 3: 1309
9d Han S, Liang A, Ren X, Gao X, Li J, Zou D, Wu Y, Wu Y. Tetrahedron Lett. 2017; 58: 4859
9e Chen C, Zeng R, Zhang J, Zhao Y. Eur. J. Org. Chem. 2017; 6947
9f Suo J.-F, Zhao X.-M, Zhang K.-X, Zhou S.-L, Niu J.-L, Song M.-P. Synthesis 2017; 49: 3916
9g Mondal S, Hajra A. Org. Biomol. Chem. 2018; 16: 2846
9h Jin C, Zhu R, Sun B, Zhang L, Zhuang X, Yu C. Asian J. Org. Chem. 2019; 8: 2213

10 Cong X, Zeng X. Org. Lett. 2014; 16: 3716
11 Reddy MD, Fronczek FR, Watkins EB. Org. Lett. 2016; 18: 5620
12 Cui M, Liu J.-H, Lu X.-Y, Lu X, Zhang Z.-Q, Xiao B, Fu Y. Tetrahedron Lett. 2017; 58: 1912
13 Niu T.-J, Xu J.-D, Ren B.-Z, Liu J.-H, Hu G.-Q. ChemistrySelect 2019; 4: 4682
14 See also: Ramesh B, Jeganmohan M. Org. Lett. 2017; 19: 6000

15a Li C.-J. Acc. Chem. Res. 2009; 42: 335
15b Ashenhurst JA. Chem. Soc. Rev. 2010; 39: 540
15c Yeung CS, Dong VM. Chem. Rev. 2011; 111: 1215
15d Liu C, Zhang H, Shi W, Lei A. Chem. Rev. 2011; 111: 1780
15e Girard SA, Knauber T, Li C.-J. Angew. Chem. Int. Ed. 2014; 53: 74
15f Liu C, Yuan J, Gao M, Tang S, Li W, Shi R, Lei A. Chem. Rev. 2015; 115: 12138
15g Kozlowski MC. Acc. Chem. Res. 2017; 50: 638
15h Huang CY, Kang H, Li J, Li CJ. J. Org. Chem. 2019; 84: 12705

Selected examples:

16a Li Z, Cao L, Li C.-J. Angew. Chem. Int. Ed. 2007; 46: 6505
16b Zhang Y, Li C.-J. Eur. J. Org. Chem. 2007; 4654
16c Tanaka T, Hashiguchi K, Tanaka T, Yazaki R, Ohshima T. ACS Catal. 2018; 8: 8430

17a Huang C.-Y, Li J, Liu W, Li C.-J. Chem. Sci. 2019; 10: 5018
17b Tian H, Yang H, Tian C, An G, Li G. Org. Lett. 2020; 22: 7709

18a Grigorjeva L, Daugulis O. Org. Lett. 2014; 16: 4688
18b Deb A, Bag S, Kancherla R, Maiti D. J. Am. Chem. Soc. 2014; 136: 13602

19 Hintermann L, Xiao L, Labonne A. Angew. Chem. Int. Ed. 2008; 47: 8246

Supplementary Material

Supporting Information (PDF) (opens in new window)