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12. For patent application of bioactive N-cyano sulfilimine and sulfoximine, see a Ahrens H. ; Braun R. ; Doerner-Rieping S. ; Koehn A. ; Lehr S. ; Dietrich H. ; Schmutzler D. ; Gatzweiler E. ; Rosinger C. H. Herbicidal 3-(sulfin-/sulfonimidoyl)？benzamides, (Bayer) . WO Patent WO2013124228A1 , 2013 . b Gnamm C. ; Oost T. Substituted pyridones and pyrazinones and their use as inhibitors of neutrophil elastase activity, (Boehringer Ingelheim) .WO Patent WO2015124563A1 , 2015 . c Oost T. ; Fiegen D. ; Gnamm C. Substituted 4-pyridones and their use as inhibitors of neutrophil elastase activity, (Boehringer Ingelheim) . WO2014029830A1 , 2014 . 

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19. a Lu K. ; Duan L. ; Xu B. ; Yin W. ; Wu D. ; Zhao Y. ; Gong P. Facile synthesis of 3-amino-5-aryl-1,2,4-oxadiazoles via PIDA-mediated intramolecular oxidative cyclization . RSC Adv. 2016 , 6 , 54277 ？ 54280 . 10.1039/C6RA08871F . b Shang X.？X. ; Vu H.？M. ; Li X.？Q. One-Pot Synthesis of 2-Arylbenzoxazinones from 2-Arylindoles with (Diacetoxyiodo)benzene as the Sole Oxidant . Synthesis 2018 , 50 , 377 ？ 383 . 10.1055/s-0036-1590933 . 

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20. UV/vis spectroscopy studies were supported this trend. In detail, please see the Supporting Information (Supporting Figure 1). 

21. Maiti S. ; Alam M. T. ; Mal P. Soft？Hard Acid？Base-Controlled C？H Trifluoroethoxylation and Trideuteriomethoxylation of Anilides . Asian J. Org. Chem. 2018 , 7 , 715 ？ 719 . 10.1002/ajoc.201800069 . 

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22. In UV/vis experiment of the mixture of Iodine (III) reagents (PIDA and PIFA) and sulfide 1 in DMF, we found that PIFA displayed a different peak pattern with PIDA case. Please see the Supporting Information (Supporting Figure 2) 

23. CCDC 1974248 ( 2a ) contain the Supporting crystallographic data for this paper. These data are provided free of by The Cambridge Crystallographic Centre. For the reported crystal structure of N -cyano sulfilimine, see a ref. 5a b Zhou S. ; Zhou S. ; Xie Y.？T. ; Jin R.？Y. ; Meng X.？D. ; Zhang D.？K. ; Hua X.？W. ; Liu M. ; Wu C.？C. ; Xiong L.？X. ; Zhao Y. ; Li Z.？M. The exploration of chiral N -cyano sulfiliminyl dicarboxamides on insecticidal activities . Chin. Chem. Lett. 2017 , 28 , 1499 ？ 1504 . 10.1016/j.cclet.2017.02.021 . 

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24. a Guo S.？R. ; Kumar P. S. ; Yuan Y.？Q. ; Yang M.？H. Gold-Catalyzed, Iodine(III)-Mediated Direct Acyloxylation of the Unactivated C(sp 3 )？H Bonds of Methyl Sulfides . Eur. J. Org. Chem. 2016 , 4260 ？ 4264 . 10.1002/ejoc.201600632 . b Zhu D. ; Chang D. ; Gan S. ; Shi L. Direct α-acyloxylation of organic sulfides with the hypervalent (diacyloxyiodo)benzene/tetra- n -butylammonium bromide (TBAB) reagent combination . RSC Adv. 2016 , 6 , 27983 ？ 27987 . 10.1039/C6RA01799A . 

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25. For the 1 H NMR study of the mixture of 2,2,2-trifluoroacetamide and PIDA in deuterated DMF, we confirmed that the proton peak corresponding to NH 2 C(O)CF 3 unchanged for over 6 h 

26. a SHIMADZU Technical information (UV) . www.Shimadzu.com/an/uv/support/ap/apl.html . b Barlin G. B. ; Riggs N. V. The reaction of phenyl iodosoacetate with N -arylacetamides . J. Chem. Soc. 1954 , 3125 ？ 3128 . 10.1039/jr9540003125 . 

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27. In details, please see the Supporting Information (Supporting Figure 3 and Table 1) 

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