Synlett 2020; 31(08): 809-812
DOI: 10.1055/s-0039-1691595
letter
© Georg Thieme Verlag Stuttgart · New York

Iminyl-Radical-Mediated Cyanoalkylarylation of Activated Alkenes Enabled by Silver-Catalyzed Decarboxylation of α-Imino Oxy Acids

Zhi Wang
,
Xiaoyu Yan
,
Xiaoxue He
,
Xinhuan Yan
,
Xiaoqing Li
,
Xiangsheng Xu
This work was supported by the National Key Research and Development Program of China (2017YFC0210900).
Further Information

Publication History

Received: 16 December 2019

Accepted after revision: 22 January 2019

Publication Date:
07 February 2020 (online)


Abstract

An iminyl-radical-mediated cyanoalkylarylation of α,β-unsaturated imides with cyclic α-imino oxy acids leading to isoquinoline-1,3(2H,4H)-dione derivatives has been developed. The procedure involves the generation of iminyl radicals through silver-catalyzed oxidative decarboxylation, followed by a C–C bond cleavage, cyanoalkylation, and C–H-functionalization cascade.

Supporting Information

 
  • References and Notes

  • 1 For a selected review, see: Morcillo SP. Angew. Chem. Int. Ed. 2019; 58: 14044

    • For selected examples, see:
    • 2a Zhang J.-J, Duan X.-H, Wu Y, Yang J.-C, Guo L.-N. Chem. Sci. 2019; 10: 161
    • 2b Wang P.-Z, Xu X.-Y, Li C.-Y, He B.-Q, Chen J.-R, Xiao W.-J. Chem. Commun. 2018; 54: 9925
    • 2c Yu X.-Y, Zhao Q.-Q, Chen J, Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed. 2018; 57: 15505
    • 2d Yu X.-Y, Chen J.-R, Wang P.-Z, Yang M.-N, Liang D, Xiao W.-J. Angew. Chem. Int. Ed. 2018; 57: 738
    • 2e Yang L, Gao P, Duan X.-H, Gu Y.-R, Guo L.-N. Org. Lett. 2018; 20: 1034
    • 2f Yin Z, Rabeah J, Brückner A, Wu X.-F. ACS Catal. 2018; 8: 10926
    • 2g Wang P.-Z, He B.-Q, Cheng Y, Chen J.-R, Xiao W.-J. Org. Lett. 2019; 21: 6924

      For reviews, see:
    • 3a Jiang H, Studer A. CCS Chem. 2019; 1: 38
    • 3b Cheng J.-R, Hu X.-Q, Lu L.-Q, Xiao W.-J. Chem. Soc. Rev. 2016; 45: 2044

    • For recent examples, see:
    • 3c Lu B, Cheng Y, Chen L.-Y, Chen J.-R, Xiao W.-J. ACS Catal. 2019; 9: 8159
    • 3d Chen J, He B.-Q, Wang P.-Z, Yu X.-Y, Zhao Q.-Q, Chen J.-R, Xiao W.-J. Org. Lett. 2019; 21: 4359
    • 3e Zhou X.-S, Cheng Y, Chen J, Yu X.-Y, Xiao W.-J, Chen J.-R. ChemCatChem 2019; 11: 5300
  • 4 Ding D, Wang C. ACS Catal. 2018; 8: 11324
    • 5a Jiang H, Studer A. Angew. Chem. Int. Ed. 2017; 56: 12273
    • 5b Davies J, Sheikh NS, Leonori D. Angew. Chem. Int. Ed. 2017; 56: 13361
    • 5c Jiang H, Studer A. Angew. Chem. Int. Ed. 2018; 57: 1692
    • 5d Hu X.-Q, Chen J.-R, Xiao W.-J. Angew. Chem. Int. Ed. 2017; 56: 1960
    • 6a Yu W, Hu P, Fan Y, Yan X, Li X, Xu X. Org. Biomol. Chem. 2015; 13: 3308
    • 6b Li X, Xu X, Hu P, Xiao X, Zhou C. J. Org. Chem. 2013; 78: 7343
    • 6c Xu X, Tang Y, Li X, Hong G, Fang M, Du X. J. Org. Chem. 2014; 79: 446
    • 7a Dauncey EM, Morcillo SP, Douglas JJ, Sheikh NS, Leonori D. Angew. Chem. Int. Ed. 2018; 57: 744
    • 7b Le Vaillant F, Garreau MS, Nicolai S, Gryn’ova G, Corminboeuf C, Waser J. Chem. Sci. 2018; 9: 5883
    • 7c Dauncey EM, Dighe SU, Douglas JJ, Leonori D. Chem. Sci. 2019; 10: 7728
  • 8 For redox-neutral cyanoalkylarylation of activated alkenes, see: Wu J, Zhang J.-Y, Gao P, Xu S.-L, Guo L.-N. J. Org. Chem. 2018; 83: 1046

    • For reviews, see:
    • 9a Yin X, Li W, Zhao B, Cheng K. Youji Huaxue 2018; 38: 2879
    • 9b Wei Y, Hu P, Zhang M, Su W. Chem. Rev. 2017; 117: 8864
    • 9c Zheng Q.-Z, Jiao N. Chem. Soc. Rev. 2016; 45: 4590

    • For our recent work, see:
    • 9d Li X, Yan X, Wang Z, He X, Dai Y, Yan X, Zhao D, Xu X. J. Org. Chem. 2020; DOI: 10.1021/acs.joc.9b03204.
  • 10 Isoquinolinediones 3as; General Procedure The appropriate N-methacryloylbenzamide 1 (0.2 mmol, 1.0 equiv), AgNO3 (6.7 mg, 20 mol%), K2S2O8 (0.6 mmol, 3.0 equiv), and oxime 2 (0.6 mmol, 3.0 equiv) were added to an oven-dried Schlenk tube. The tube was evacuated and backfilled with argon three times, and then MeCN (2.0 mL) was injected into the tube from a syringe. The mixture was stirred at 90 °C (block heater) for 20 h. The resulting mixture was diluted with EtOAc, and the organic phase was washed successively with H2O (×3) and brine (×1) then dried (Na2SO4) and concentrated in vacuo. The residue was purified by column chromatography [silica gel, EtOAc–PE (gradient 1:10 to 1:4)]. 5-(2,4-Dimethyl-1,3-dioxo-1,2,3,4-tetrahydroisoquinolin-4-yl)pentanenitrile (3a) Pale-yellow oil; yield: 44.1 mg (82%); Rf  = 0.32 (EtOAc–PE, 1:4). 1H NMR (500 MHz, CDCl3): δ = 8.25 (dd, J = 8.0, 1.3 Hz, 1 H), 7.68–7.64 (m, 1 H), 7.47–7.40 (m, 2 H), 3.39 (s, 3 H), 2.36–2.30 (m, 1 H), 2.22–2.17 (m, 2 H), 1.93–1.89 (m, 1 H), 1.61 (s, 3 H), 1.55–1.51 (m, 2 H), 1.05–1.02 (m, 1 H), 0.94–0.92 (m, 1 H). 13C NMR (125 MHz, CDCl3): δ = 176.3, 164.2, 143.0, 134.2, 129.0, 127.5, 125.0, 124.8, 119.1, 47.5, 41.6, 29.7, 27.1, 25.2, 24.4, 16.7. HRMS (ESI): m/z [M + H]+ calcd for C16H19N2O2 +: 271.1441; found: 271.1446.
    • 11a Xu Z, Jia R, Ma Z, Cao S, Shen L, Ji H. Synlett 2019; 30: 1909
    • 11b Xia X.-F, Zhu S.-L, Liu J.-B, Wang D, Liang Y.-M. J. Org. Chem. 2016; 81: 12482
    • 11c Tang S, Deng Y.-L, Li J, Wang W.-X, Wang Y.-C, Li Z.-Z, Yuan L, Chen S.-L, Sheng R.-L. Chem. Commun. 2016; 52: 4470
    • 11d Tang S, Deng Y.-L, Li J, Wang W.-X, Ding G.-L, Wang M.-W, Xiao Z.-P, Wang Y.-C, Sheng R.-L. J. Org. Chem. 2015; 80: 12599
    • 11e Zhang M, Xie P, Zhao W, Niu B, Wu W, Bian Z, Pittman CU. Jr, Zhou A. J. Org. Chem. 2015; 80: 4176
    • 11f Wei Y.-L, Chen J.-Q, Sun B, Xu P.-F. Chem. Commun. 2019; 55: 5922