Synthesis 2019; 51(21): 4078-4084
DOI: 10.1055/s-0039-1690178
paper
© Georg Thieme Verlag Stuttgart · New York

A Straightforward Conversion of Activated Amides and Haloalkanes into Esters under Transition-Metal-Free Cs2CO3/DMAP Conditions

Junsheng Jian
,
Zijia Wang
School of Chemistry and Environment, South China Normal University, Guangzhou, P. R. of China   Email: wslnwzj@foxmail.com   Email: zhuoz@scnu.edu.cn
,
Liuqing Chen
,
Ying Gu
,
Liqiong Miao
,
Yueping Liu
,
Zhuo Zeng
School of Chemistry and Environment, South China Normal University, Guangzhou, P. R. of China   Email: wslnwzj@foxmail.com   Email: zhuoz@scnu.edu.cn
› Author Affiliations
The authors gratefully acknowledge the support of Science and Technology Planning Project of Guangdong Province (2017A010103017), Special Innovation Projects of Common Universities in Guangdong Province (20178S0182), National Natural Science Foundation of China (21272080).
Further Information

Publication History

Received: 03 April 2019

Accepted after revision: 24 July 2019

Publication Date:
14 August 2019 (eFirst)

Abstract

The esterification of activated amides, N-acylsaccharins, under transition-metal-free conditions with good functional group tolerance has been developed, resulting in C–N cleavage leading to efficient synthesis of a variety of esters in moderate to good yields. This work demonstrates that esterification may proceed by using simple N-acylsaccharins, haloalkanes, and Cs2CO3 as oxygen source.

Supporting Information

 
  • References

    • 1a Brink G.-J, Arends IW. C. E, Sheldon RA. Chem. Rev. 2004; 104: 4105
    • 1b Yang N, Su Z, Feng X, Hu C. Chem. Eur. J. 2015; 21: 7264
    • 1c Shimizu N, Sakata D, Schmelz EA, Mori N, Kuwahara Y. Proc. Natl. Acad. Sci. U.S.A. 2017; 11: 2616
  • 2 Gopinath R, Patel BK. Org. Lett. 2000; 2: 577
  • 3 Enders D, Balensiefer T. Acc. Chem. Res. 2004; 37: 534
  • 4 Kiyooka S, Wada Y, Ueno M, Yokoyama T, Yokoyama R. Tetrahedron 2007; 63: 12695
  • 5 Konakahara T, Kiran Y, Ikeda R, Sakai N. Synthesis 2010; 276
    • 6a Dick AR, Hull KL, Sanford MS. J. Am. Chem. Soc. 2004; 126: 2300
    • 6b Desai LV, Hull KL, Sanford MS. J. Am. Chem. Soc. 2004; 126: 9542
    • 6c Chen X, Hao X.-S, Goodhue CE, Yu J.-Q. J. Am. Chem. Soc. 2006; 128: 6790
    • 6d Kano T, Mii H, Maruoka K. J. Am. Chem. Soc. 2009; 131: 3450
    • 6e Wang Z, Kuninobu Y, Kanai M. Org. Lett. 2014; 16: 4790
    • 6f Raghuvanshi K, Rauch K, Ackermann L. Chem. Eur. J. 2015; 21: 1790
    • 7a Ouyang K, Hao W, Zhang WX, Xi Z. Chem. Rev. 2015; 115: 12045
    • 7b Takise R, Muto K, Yamaguchi J. Chem. Soc. Rev. 2017; 46: 5864
    • 7c Shi S, Nolan SP, Szostak M. Acc. Chem. Res. 2018; 51: 2589
    • 7d Meng G, Szostak M. Eur. J. Org. Chem. 2018; 2352
    • 7e Buchspies J, Szostak M. Catalysts 2019; 9: 53
    • 8a Hie L, Nathel NF. F, Shah TK, Baker EL, Hong X, Yang Y.-F, Liu P, Houk KN, Garg NK. Nature 2015; 524: 79
    • 8b Baker EL, Yamano MM, Zhou Y, Anthony SM, Garg NK. Nat. Commun. 2016; 7: 11554
    • 8c Dander JE, Weires NA, Garg NK. Org. Lett. 2016; 18: 3934
    • 8d Hie LE, Baker L, Anthony SM, Desrosiers JN, Senanayake C, Garg NK. Angew. Chem. Int. Ed. 2016; 55: 15129
    • 8e Weires NA, Baker EL, Garg NK. Nat. Chem. 2016; 8: 75
    • 8f Dander JE, Baker EL, Garg NK. Chem. Sci. 2017; 8: 6433
    • 8g Meng G, Lalancette R, Szostak R, Szostak M. Org. Lett. 2017; 19: 4656
    • 8h Branchu Y, Gosmini C, Danoun G. Chem. Eur. J. 2017; 23: 10043
    • 8i Liu Y, Shi S, Achtenhagen M, Liu R, Szostak M. Org. Lett. 2017; 19: 1614
    • 8j Li G, Szostak M. Nat. Commun. 2018; 9: 4165
    • 8k Liu Y, Achtenhagen M, Liu R, Szostak M. Org. Biomol. Chem. 2018; 16: 1322
    • 8l Boit TB, Weires NA, Kim J, Garg NK. ACS Catal. 2018; 8: 1003
    • 8m Chen C, Liu P, Luo M, Zeng X. ACS Catal. 2018; 8: 5864
  • 9 Li G, Lei P, Szostak M. Org. Lett. 2018; 20: 5622
    • 10a Ren L, Wang L, Lv Y, Li G, Gao S. Org. Lett. 2015; 17: 5172
    • 10b Wang L, Li J, Dai W, Lv Y, Zhang Y, Gao S. Green Chem. 2014; 16: 2164
    • 11a Ueno S, Chatani N, Kakiuchi F. J. Am. Chem. Soc. 2007; 129: 6098
    • 11b Tobisu M, Nakamura K, Chatani N. J. Am. Chem. Soc. 2014; 136: 5587
    • 11c Liu C, Meng G, Szostak M. J. Org. Chem. 2016; 81: 12023
    • 11d Liu C, Meng G, Liu Y, Liu R, Lalancette R, Szostak R, Szostak M. Org. Lett. 2016; 18: 4194
    • 11e Shi S, Meng G, Szostak M. Angew. Chem. Int. Ed. 2016; 55: 6959
    • 11f Liu Y, Liu R, Szostak M. Org. Biomol. Chem. 2017; 15: 1780
    • 11g Cong X, Fan F, Ma P, Luo M, Chen H, Zeng X. J. Am. Chem. Soc. 2017; 139: 15182
    • 11h Szostak R, Liu C, Lalancette R, Szostak M. J. Org. Chem. 2018; 83: 14676
    • 12a Cui M, Wu H, Jian J, Wang H, Liu C, Daniel S, Zeng Z. Chem. Commun. 2016; 52: 2076
    • 12b Wu H, Li Y, Cui M, Jian J, Zeng Z. Adv. Synth. Catal. 2016; 358: 3876
    • 12c Wu H, Liu T, Cui M, Li Y, Jian J, Wang H, Zeng Z. Org. Biomol. Chem. 2017; 15: 536
    • 12d Cui M, Chen Z, Liu T, Wang H, Zeng Z. Tetrahedron Lett. 2017; 58: 3819
    • 12e Wu H, Guo W, Daniel S, Li Y, Liu C, Zeng Z. Chem. Eur. J. 2018; 24: 3444
    • 12f Luo Z, Liu T, Guo W, Wang Z, Huang J, Zhu Y, Zeng Z. Org. Process Res. Dev. 2018; 22: 1188
    • 12g Guo W, Huang J, Wu H, Liu T, Luo Z, Jian J, Zeng Z. Org. Chem. Front. 2018; 5: 2950