Synthesis 2020; 52(20): 3065-3070
DOI: 10.1055/s-0040-1707186
paper
© Georg Thieme Verlag Stuttgart · New York

Metal-Free Insertion of Sulfoxonium Ylides into Arylamines in Water

Hua He
a  West China Hospital, Sichuan University, Chengdu, 610041, P. R. of China   Email: 413046786@qq.com
b  Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China   Email: wyong@scu.edu.cn
,
Kaichuan Yan
b  Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China   Email: wyong@scu.edu.cn
,
Jianglian Li
b  Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China   Email: wyong@scu.edu.cn
,
Ruizhi Lai
b  Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China   Email: wyong@scu.edu.cn
,
Yi Luo
b  Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China   Email: wyong@scu.edu.cn
,
Mei Guan
a  West China Hospital, Sichuan University, Chengdu, 610041, P. R. of China   Email: 413046786@qq.com
,
Yong Wu
b  Key Laboratory of Drug-Targeting and Drug Delivery System of the Education Ministry and Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, No. 17 Southern Renmin Road, Chengdu, Sichuan 610041, P. R. of China   Email: wyong@scu.edu.cn
› Author Affiliations
This work was supported by the National Natural Science Foundation of China (grant numbers 81573286 and 81373259).
Further Information

Publication History

Received: 25 May 2020

Accepted after revision: 12 June 2020

Publication Date:
21 July 2020 (online)


Abstract

Carbenoid-based N–H insertions have undergone significant development with respect to C–N bond formation in recent years. However, the existing methods suffer from unstable starting materials, expensive metal catalysts and organic solvents. Herein, insertion of sulfoxonium ylides into arylamines under metal-free conditions has been developed. The method employs water as solvent at mild temperature and is amenable to the late-stage modification of structurally complex bioactive compounds.

Supporting Information

 
  • References

    • 2a Ullmann F. Ber. Dtsch. Chem. Ges. 1903; 36: 2382
    • 2b Goldberg I. Ber. Dtsch. Chem. Ges. 1906; 39: 1691
    • 2c Bariwal J, van der Eycken E. Chem. Soc. Rev. 2013; 42: 9283
    • 2d Bhunia S, Pawar GG, Kumar SV, Jiang Y, Ma D. Angew. Chem. Int. Ed. 2017; 56: 16136
    • 2e Coman SM, Parvulescu VI. Org. Process Res. Dev. 2015; 19: 1327
    • 2f R.-C., P., Buchwald S. L.; Chem. Rev.; 2016, 116: 12564
    • 3a Gillingham D, Fei N. Chem. Soc. Rev. 2013; 42: 4918
    • 3b Abu-Elfotoh A.-M. Tetrahedron Lett. 2017; 58: 4750
    • 3c Arredondo VS, Hiew C, Gutman ES, Premachandra ID, Van Vranken DL. Angew. Chem. Int. Ed. 2017; 56: 4156
    • 3d Aviv I, Gross Z. Chem. Eur. J. 2008; 14: 3995
    • 3e Luo H, Wu G, Zhang Y, Wang J. Angew. Chem. Int. Ed. 2015; 54: 14503
    • 3f Sreenilayam G, Fasan R. Chem. Commun. 2015; 51: 1532
    • 3g Zhu Y, Liu X, Dong S, Zhou Y, Li W, Lin L, Feng X. Angew. Chem. Int. Ed. 2014; 53: 1636
    • 4a Jia M, Ma S. Angew. Chem. Int. Ed. 2016; 55: 9134
    • 4b Xia Y, Wang J. Chem. Soc. Rev. 2017; 46: 2306
  • 5 Ingold CK, Jessop JA. J. Chem. Soc. 1930; 713
    • 6a Li A.-H, Dai L.-X, Aggarwal VK. Chem. Rev. 1997; 97: 2341
    • 6b Aggarwal VK, Winn CL. Acc. Chem. Res. 2004; 37: 611
    • 6c Kaiser D, Klose I, Oost R, Neuhaus J, Maulide N. Chem. Rev. 2019; 119: 8701
    • 6d Lu L.-Q, Li T.-R, Wang Q, Xiao W.-J. Chem. Soc. Rev. 2017; 46: 4135
    • 6e Xia X.-D, Lu L.-Q, Liu W.-Q, Chen D.-Z, Zheng Y.-H, Wu L.-Z, Xiao W.-J. Chem. Eur. J. 2016; 22: 8432
    • 7a Bayer A, Vaitla J. Synthesis 2018; 51: 612
    • 7b Burtoloso AC. B, Dias RM. P, Leonarczyk IA. Eur. J. Org. Chem. 2013; 5005
    • 8a Baldwin JE, Adlington RM, Godfrey CR. A, Gollins DW, Vaughan JG. J. Chem. Soc., Chem. Commun. 1993; 1434
    • 8b Mangion IK, Nwamba IK, Shevlin M, Huffman MA. Org. Lett. 2009; 11: 3566
    • 9a Mangion IK, Ruck RT, Rivera N, Huffman MA, Shevlin M. Org. Lett. 2011; 13: 5480
    • 9b Mangion IK, Weisel M. Tetrahedron Lett. 2010; 51: 5490
    • 9c Phelps AM, Chan VS, Napolitano JG, Krabbe SW, Schomaker JM, Shekhar S. J. Org. Chem. 2016; 81: 4158
    • 9d Vaitla J, Bayer A, Hopmann KH. Angew. Chem. Int. Ed. 2017; 56: 4277
  • 10 Dias RM, Burtoloso AC. Org. Lett. 2016; 18: 3034
    • 11a Ball ZT. Acc. Chem. Res. 2013; 46: 560
    • 11b Chen Z, Popp BV, Bovet CL, Ball ZT. ACS Chem. Biol. 2011; 6: 920
    • 11c Chen Z, Vohidov F, Coughlin JM, Stagg LJ, Arold ST. J. Am. Chem. Soc. 2012; 134: 10138
    • 11d Antos JM, McFarland JM, Iavarone AT, Francis MB. J. Am. Chem. Soc. 2009; 131: 6301
    • 11e Sreenilayam G, Fasan R. Chem. Commun. 2015; 51: 1532
    • 11f Tishinov K, Schmidt K, Haussinger D, Gillingham DG. Angew. Chem. Int. Ed. 2012; 51: 12000
  • 12 Konig H, Metzger H. Chem. Ber. 1965; 98: 3733