Synthesis, Inhaltsverzeichnis Synthesis 2021; 53(20): 3744-3750DOI: 10.1055/a-1493-6885 feature N-Selenocyanato-Dibenzenesulfonimide: A New Electrophilic Selenocyanation Reagent Deng Zhu , Ai-Hui Ye , Zhi-Min Chen ∗ Artikel empfehlen Abstract Artikel einzeln kaufen Alle Artikel dieser Rubrik Abstract A new electrophilic selenocyanation reagent N-selenocyanato-dibenzenesulfonimide was readily prepared in two steps from commercially available dibenzenesulfonimide for the first time. A variety of electrophilic selenocyanato reactions of nucleophiles have been achieved using it as selenocyanato source under mild and simple conditions. Numerous SeCN-containing compounds were obtained in moderate to excellent yields. Meanwhile, a Lewis acid mediated tandem selenocyanation/cyclization reaction of alkenes with phenols, which provided simple methods for the formation of various SeCN-containing chromanes and dihydrobenzofurans in moderate to good yields, has also been developed. Key words Key words N-selenocyanato-dibenzenesulfonimide - electrophilic selenocyanation - chromane - dihydrobenzofuran - organoselenium compound Volltext Referenzen References 1a Tang Q, Bian Z, Wu W, Wang J, Xie P, Pittman CU, Zhou A. J. Org. Chem. 2017; 82: 10622 1b Weekley CM, Harris HH. Chem. Soc. Rev. 2013; 42: 8870 1c Mugesh G, Singh HB. Chem. Soc. Rev. 2000; 29: 347 2a Wang X.-Y, Zhong Y.-F, Mo Z.-Y, Wu S.-H, Xu Y.-L, Tang H.-T, Pan Y.-M. Adv. Synth. Catal. 2021; 363: 208 2b Liu H.-Y, Zhang J.-R, Huang G.-B, Zhou Y.-H, Chen Y.-Y, Xu Y.-L. Adv. Synth. Catal. 2021; 363: 1656 2c Meng X.-J, Zhong P.-F, Wang Y.-M, Wang H.-S, Tang H.-T, Pan Y.-M. Adv. Synth. Catal. 2020; 362: 506 2d Sun L, Yuan Y, Yao M, Wang H, Wang D, Gao M, Chen Y.-H, Lei A. Org. Lett. 2019; 21: 1297 2e Guan Z, Wang Y, Wang H, Huang Y, Wang S, Tang H, Zhang H, Lei A. Green Chem. 2019; 21: 4976 2f Zhang X, Wang C, Jiang H, Sun L. RSC Adv. 2018; 8: 22042 2g Martins IL, Charneira C, Gandin V, Ferreira Da Silva JL, Justino GC, Telo JP, Vieira AJ. S. C, Marzano C, Antunes AM. M. J. Med. Chem. 2015; 58: 4250 2h Nogueira CW, Zeni G, Rocha JB. T. Chem. Rev. 2004; 104: 6255 3a Sun K, Lv Y, Chen Y, Zhou T, Xing Y, Wang X. Org. Biomol. Chem. 2017; 15: 4464 3b Maity P, Paroi B, Ranu BC. Org. Lett. 2017; 19: 5748 3c Wang Z, Ji X, Hu M, Tang R. Tetrahedron Lett. 2015; 56: 5067 3d Singha Roy S, Ghosh P, Hossain SkU, Chakraborty P, Biswas J, Mandal S, Bhattacharjee A, Bhattacharya S. Bioorg. Med. Chem. Lett. 2010; 20: 6951 3e Prakash O, Rani N, Sharma V, Moriarty RM. Synlett 1997; 1255 4 Plano D, Karelia DN, Pandey MK, Spallholz JE, Amin S, Sharma AK. J. Med. Chem. 2016; 59: 1946 5a Mukherjee N, Kundu D, Ranu BC. Adv. Synth. Catal. 2017; 359: 329 5b Guan Y, Townsend SD. Org. Lett. 2017; 19: 5252 5c Krief A, Dumont W, Delmotte C. Angew. Chem. Int. Ed. 2000; 39: 1669 5d Krief A, Delmotte C, Dumont W. Tetrahedron 1997; 53: 12147 For selected examples, see: 6a Guo W, Tan W, Zhao M, Zheng L, Tao K, Chen D, Fan X. J. Org. Chem. 2018; 83: 6580 6b Frei R, Courant T, Wodrich MD, Waser J. Chem. Eur. J. 2015; 21: 2662 6c Feng C, Peng Y, Ding G, Li X, Cui C, Yan Y. Chem. Commun. 2018; 54: 13367 6d Redon S, Kosso AR. O, Broggi J, Vanelle P. Tetrahedron Lett. 2017; 58: 2771 6e Redon S, Kosso AR. O, Broggi J, Vanelle P. Synthesis 2019; 51: 3758 7a Gao M, Vuagnat M, Chen M.-Y, Pannecoucke X, Jubault P, Besset T. Chem. Eur. J. 2021; 27: 6145 7b Xiao J.-A, Li Y.-C, Cheng X.-L, Chen W.-Q, Cui J, Huang Y, Huang J, Xiao Q, Su W, Yang H. Org. Chem. Front. 2019; 6: 1967 7c Wu D, Qiu J, Li C, Yuan L, Yin H, Chen F.-X. J. Org. Chem. 2020; 85: 934 7d Xiao J.-A, Cheng X.-L, Meng R.-F, Qin X.-S, Peng H, Ren J.-W, Xie Z.-Z, Cui J.-G, Huang Y.-M. Synthesis 2021; 53: 954 8a Xie Y.-Y, Chen Z.-M, Luo H.-Y, Shao H, Tu Y.-Q, Bao X.-G, Cao R.-F, Zhang S.-Y, Tian J.-M. Angew. Chem. Int. Ed. 2019; 58: 12491 8b Luo H.-Y, Xie Y.-Y, Song X.-F, Dong J.-W, Zhu D, Chen Z.-M. Chem. Commun. 2019; 55: 9367 8c Luo H.-Y, Dong J.-W, Xie Y.-Y, Song X.-F, Zhu D, Ding T.-M, Liu Y.-Y, Chen Z.-M. Chem. Eur. J. 2019; 25: 15411 8d Song X.-F, Ye A.-H, Xie Y.-Y, Dong J.-W, Chen C, Zhang Y, Chen Z.-M. Org. Lett. 2019; 21: 9550 8e Song X.-F, Ding T.-M, Zhu D, Huang J, Chen Z.-M. Org. Lett. 2020; 22: 7052 9a Ye A.-H, Zhang Y, Xie Y.-Y, Luo H.-Y, Dong J.-W, Liu X.-D, Song X.-F, Ding T.-M, Chen Z.-M. Org. Lett. 2019; 21: 5106 9b Li C, Long P, Wu H, Yin H, Chen F.-X. Org. Biomol. Chem. 2019; 17: 7131 10 CCDC 2061576 (1d) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures 11 CCDC 2073817 (5d) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures Zusatzmaterial Zusatzmaterial Supporting Information
