Synthesis 2019; 51(13): 2697-2704
DOI: 10.1055/s-0037-1610705
special topic
© Georg Thieme Verlag Stuttgart · New York

Silver-Catalyzed para-Selective C–H Amination of 1-Naphthyl­amides with Azodicarboxylates at Room Temperature

Quan-Zhe Li
a  Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
Xun-Hui Wang
a  Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
Si-Hua Hou
a  Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
Yan-Yan Ma
b  School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, P. R. China
,
Deng-Gao Zhao
b  School of Biotechnology and Health Sciences, Wuyi University, Jiangmen 529020, P. R. China
,
a  Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
He-Yuan Bai*
a  Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
,
Tong-Mei Ding*
a  Shanghai Key Laboratory for Molecular Engineering of Chiral Drugs & School of Chemistry and Chemical Engineering, Shanghai Jiao Tong University, Shanghai 200240, P. R. China   Email: dtm@sjtu.edu.cn   Email: baiheyuan90@sjtu.edu.cn
› Author Affiliations
This work was supported by the NSFC (No. 21672145, No. 21602131), Shanghai Jiao Tong University (No. ZH2018QNA44, No. IPP18080) and Department of Education of Guangdong Province (No. 2016KTSCX140).
Further Information

Publication History

Received: 13 February 2019

Accepted after revision: 19 March 2019

Publication Date:
11 April 2019 (eFirst)

Published as part of the Special Topic Amination Reactions in Organic Synthesis

Abstract

A simple and efficient protocol for para-selective C–H amination of 1-naphthylamide derivatives under silver catalysis is described. This reaction system could proceed without the help of directing group and a broad range of substrates were proved to be well tolerated. In addition, control experiments suggested that this reaction might not proceed via a single-electron-transfer process.

Supporting Information

 
  • References


    • For recent reviews, see:
    • 1a Godula K, Sames D. Science 2006; 312: 67
    • 1b Beccalli EM, Broggini G, Martinelli M, Sottocornola S. Chem. Rev. 2007; 107: 5318
    • 1c Davies HM. L, Manning JR. Nature 2008; 451: 417
    • 1d Lyons TW, Sanford MS. Chem. Rev. 2010; 110: 1147
    • 1e Cho SH, Kim JY, Kwak J, Chang S. Chem. Soc. Rev. 2011; 40: 5068
    • 1f Song G.-Y, Wang F, Li X.-W. Chem. Soc. Rev. 2012; 41: 3651
    • 1g Bariwal J, Van der Eycken E. Chem. Soc. Rev. 2013; 42: 9283
    • 1h Louillat ML, Patureau FW. Chem. Soc. Rev. 2014; 43: 901
    • 1i Wan J.-P, Jing Y. Beilstein J. Org. Chem. 2015; 11: 2209
    • 1j Subramanian P, Rudolf GC, Kaliappan KP. Chem. Asian J. 2016; 11: 168
    • 1k Yu S, Tang G, Li Y, Zhou X, Lan Y, Li X. Angew. Chem. Int. Ed. 2016; 55: 8696
    • 1l Jiao J, Murakami K, Itami K. ACS Catal. 2016; 6: 610
    • 1m Kim H, Chang S. ACS Catal. 2016; 6: 2341
    • 1n Rit RK, Shankara M, Sahoo AK. Org. Biomol. Chem. 2017; 15: 1282
    • 1o Park Y, Kim Y, Chang S. Chem. Rev. 2017; 117: 9247
    • 2a Rinehart KL. Jr. Acc. Chem. Res. 1972; 5: 57
    • 2b Medarde M, Maya AB. S, Perez-Melero CJ. Enzyme Inhib. Med. Chem. 2004; 19: 521
    • 2c Ukita T, Nakamura Y, Kubo A, Yamamoto Y, Takahashi M, Kotera J, Ikeo T. J. Med. Chem. 1999; 42: 1293
    • 2d Jiang ZY, Xu LL, Lu MC, Chen ZY, Yuan ZW, Xu XL, Guo XK, Zhang XJ, Sun HP, You QD. J. Med. Chem. 2015; 58: 6410
    • 2e Lu M.-C, Zhou H.-S, You Q.-D, Jiang Z.-G. J. Med. Chem. 2016; 59: 7305

      For selected examples for direct C–H functionalization of naphthalene derivatives, see:
    • 3a Mal D, Pahari P. Chem. Rev. 2007; 107: 1892
    • 3b Stuart DR, Bertrand-Laperle M, Burgess KM. N, Fagnou K. J. Am. Chem. Soc. 2008; 130: 16474
    • 3c Van Otterlo WA. L, de Koning CB. Chem. Rev. 2009; 109: 3743
    • 3d Wang C, Chen H, Wang Z, Chen J, Huang Y. Angew. Chem. Int. Ed. 2012; 51: 7242
    • 3e Ju L, Yao J, Wu Z, Liu Z, Zhang Y. J. Org. Chem. 2013; 78: 10821
    • 3f Tran ND. M, Zard SZ. Org. Biomol. Chem. 2014; 12: 3251
    • 3g Kondrashov M, Raman S, Wendt OF. Chem. Commun. 2015; 51: 911
    • 3h Moghaddam FM, Tavakoli G, Saeednia B, Langer P, Jafari B. J. Org. Chem. 2016; 81: 3868

      For o-C–H functionalizations of naphthalene derivatives, see:
    • 4a Iwasaki M, Iyanaga M, Tsuchiya Y, Nishimura Y, Li W, Li Z, Nishihara Y. Chem. Eur. J. 2014; 20: 2459
    • 4b Martinez AM, Rodriguez N, Arrayas RG, Carretero JC. Chem. Commun. 2014; 50: 2801
    • 4c Zhang X, Si W, Bao M, Asao N, Yamamoto Y, Jin T. Org. Lett. 2014; 16: 4830
    • 4d Kondrashov M, Raman S, Wendt OF. Chem. Commun. 2015; 51: 911

      For C8–H functionalization of naphthalene derivatives, see:
    • 5a Ng K.-H, Chan AS. C, Yu W.-Y. J. Am. Chem. Soc. 2010; 132: 12862
    • 5b Li X.-T, Gong X, Zhao M, Song G.-Y, Deng J, Li X.-W. Org. Lett. 2011; 13: 5808
    • 5c Huang LH, Li Q, Wang C, Qi CZ. J. Org. Chem. 2013; 78: 3030
    • 5d Odani R, Hirano K, Satoh T, Miura M. J. Org. Chem. 2013; 78: 11045
    • 5e Iwasaki M, Kaneshika W, Tsuchiya Y, Nakajima K, Nishihara Y. J. Org. Chem. 2014; 79: 11330
    • 5f Shang R, Ilies L, Nakamura E. J. Am. Chem. Soc. 2015; 137: 7660
    • 5g Wang L.-L, Yang M.-X, Liu X.-C, Song H, Han L, Chu WY, Sun Z.-Z. Appl. Organomet. Chem. 2016; 30: 680
    • 5h Li Z.-X, Sun S.-Y, Qiao H.-J, Yang F, Zhu Y, Kang J.-X, Wu Y.-S, Wu Y.-J. Org. Lett. 2016; 18: 4594
    • 5i Lan J.-Y, Xie H.-S, Lu X.-X, Deng Y.-F, Jiang H.-F, Zeng W. Org. Lett. 2017; 19: 4279
  • 6 Li J.-M, Wang Y.-H, Yu Y, Wu R.-B, Weng J, Lu G. ACS Catal. 2017; 7: 2661
  • 7 Bai P.-R, Sun S.-Y, Li Z.-X, Qiao H.-J, Su X.-X, Yang F, Wu Y.-S, Wu Y.-J. J. Org. Chem. 2017; 82: 12119
  • 8 Zhu H.-M, Sun S.-Y, Qiao H.-J, Yang F, Kang J.-X, Wu Y.-S, Wu Y.-J. Org. Lett. 2018; 20: 620
    • 9a Jenkins TJ, Guan B, Dai M, Li G, Lightburn TE, Huang S, Freeze BS, Burdi DF, Jacutin-Porte S, Bennett R, Chen W, Minor C, Ghosh S, Blackburn C, Gigstad KM, Jones M, Kolbeck R, Yin W, Smith S, Cardillo D, Ocain TD, Harriman GC. J. Med. Chem. 2007; 50: 566
    • 9b Abulwerdi FA, Liao C, Mady A, Gavin J, Shen C, Cierpicki T, Stuckey JA, Showalter HD. H, Nikolovska-Coleska Z. J. Med. Chem. 2014; 57: 4111
    • 9c Lee M, Rangisetty JB, Pullagurla MR, Dukat M, Setola V, Roth BL, Glennon RA. Bioorg. Med. Chem. Lett. 2005; 15: 1707

      For selected examples of C–N bond formation using azodicarboxylates, see:
    • 10a Evans DA, Nelson SG. J. Am. Chem. Soc. 1997; 119 6452
    • 10b List B. J. Am. Chem. Soc. 2002; 124: 5656
    • 10c Poulsen TB, Alemparte C, Jørgensen KA. J. Am. Chem. Soc. 2005; 127: 11614
    • 10d Suri JT, Steiner DD, Barbas CF. Org. Lett. 2005; 7: 3885
    • 10e Muñiz K, Iglesias A. Angew. Chem. Int. Ed. 2007; 46: 6350
    • 10f Gu L, Neo B, Zhang S.-Y. Org. Lett. 2011; 13: 1872
    • 10g Yang X, Toste FD. J. Am. Chem. Soc. 2015; 137: 3205
    • 10h Wang S.-G, Yin Q, Zhou C.-X, You S.-L. Angew. Chem. Int. Ed. 2015; 54: 647
    • 11a Bai H.-Y, Ma Z.-G, Yi M, Lin J.-B, Zhang S.-Y. ACS Catal. 2017; 7: 2042
    • 11b Zhang T.-Y, Lin J.-B, Li Q.-Z, Kang J.-C, Pan J.-L, Hou S.-H, Chen C, Zhang S.-Y. Org. Lett. 2017; 19: 1764
    • 11c Zhang T.-Y, Liu C, Chen C, Liu J.-X, Xiang H.-Y, Jiang W, Ding T.-M, Zhang S.-Y. Org. Lett. 2018; 20: 220
    • 11d Ding J, Jiang W, Bai H.-Y, Ding T.-M, Gao D.-F, Bao X.-G, Zhang S.-Y. Chem.Commun. 2018; 54: 8889
    • 11e Dong J-W, Ding T.-M, Zhang S.-Y, Chen Z.-M, Tu Y.-Q. Angew. Chem. Int. Ed. 2018; 130: 13376
    • 11f Fu X, Bai H.-Y, Zhu G.-D, Huang Y, Zhang S.-Y. Org. Lett. 2018; 20: 3469
    • 11g Bai H.-Y, Fu X, Pan J.-L, Ma H.-Q, Chen Z.-M, Ding T.-M, Zhang S.-Y. Adv. Synth. Catal. 2018; 360: 4205
    • 12a Shan G, Yang X.-L, Zong Y, Rao Y. Angew. Chem. Int. Ed. 2013; 52: 13606
    • 12b Yang X.-L, Sun Y.-H, Sun T.-Y, Rao Y. Chem. Commun. 2016; 52: 6423
    • 12c Long A, Gurrala SR. Patent PCT Int. Appl. 2015179414, 2015
    • 12d Chen Y.-H, Qi L.-W, Fang F, Tan B. Angew. Chem. Int. Ed. 2017; 56: 16038