Synthesis, Inhaltsverzeichnis Synthesis 2021; 53(16): 2889-2896DOI: 10.1055/a-1488-4467 paper Yb(OTf)3-Mediated Regioselective Hydroamination of Ynamides with Anilines and p-Toluenesulfonamide Autor*innen Xiaobao Zeng ∗ Qingyun Gu Wenjing Dai Yushan Xie Xinyi Liu Guixia Wu Artikel empfehlen Abstract Artikel einzeln kaufen(opens in new window) Alle Artikel dieser Rubrik(opens in new window) Abstract A rare-earth salt Yb(OTf)3-catalyzed regioselective hydroamination of ynamides with anilines and p-toluenesulfonamide has been developed. This protocol provided facile access to a diverse range of amidines with good functional group tolerance in moderate to high yields. Key words Key wordsrare-earth salts - hydroamination - ynamides - amidines - amide Volltext Referenzen References 1a Wu W, Jiang H. Acc. Chem. Res. 2014; 47: 2483 1b Minehan TG. Acc. Chem. Res. 2016; 49: 1168 1c Gabriele B, Mancuso R, Larock RC. Curr. Org. Chem. 2014; 18: 341 1d Campeau D, LeónRayo DF, Mansour A, Muratov K, Gagosz F. Chem. Rev. 2020; 120 in press 1e Bag D, Sawant SD. Chem. Eur. J. 2021; 27: 1165 1f Suleymanov AA, Severin K. Angew. Chem. Int. Ed. 2021; 60: 6879 1g Hari DP, Caramenti P, Waser J. Acc. Chem. Res. 2018; 51: 3212 For selected review in ynamides, see: 2a DeKorver KA, Li H, Lohse AG, Hayashi R, Lu Z, Zhang Y, Hsung RP. Chem. Rev. 2010; 110: 5064 2b Wang X.-N, Yeom H.-S, Fang L.-C, He S, Ma Z.-X, Kedrowski BL, Hsung RP. Acc. Chem. Res. 2014; 47: 560 2c Chen Y.-B, Qian P.-C, Ye L.-W. Chem. Soc. Rev. 2020; 49: 8897 2d Hong F.-L, Ye L.-W. Acc. Chem. Res. 2020; 53: 2003 2e Luo J, Chen G.-S, Chen S.-J, Yu J.-S, Li Z.-D, Liu Y.-L. ACS Catal. 2020; 10: 13978 2f Lynch CC, Sripada A, Wolf C. Chem. Soc. Rev. 2020; 49: 8543 2g Mahe C, Cariou K. Adv. Synth. Catal. 2020; 362: 4820 2h Hu Y.-C, Zhao Y, Wan B, Chen Q.-A. Chem. Soc. Rev. 2021; 50: 2582 2i Tan T.-D, Wang Z.-S, Qian P.-C, Ye L.-W. Small Methods 2021; 5: in press 2j Madelaine C, Valerio V, Maulide N. Chem. Asian J. 2011; 6: 2224 2k Evano G, Coste A, Jouvin K. Angew. Chem. Int. Ed. 2010; 49: 2840 2l Dodd RH, Cariou K. Chem. Eur. J. 2018; 24: 2297 2m Zhou B, Tan T.-D, Zhu X.-Q, Shang M, Ye L.-W. ACS Catal. 2019; 9: 6393 For selected examples, see: 3a Li L, Chen X.-M, Wang Z.-S, Zhou B, Liu X, Lu X, Ye L.-W. ACS Catal. 2017; 7: 4004 3b Frischmuth A, Knochel P. Angew. Chem. Int. Ed. 2013; 52: 10084 3c Xu W, Chen Y, Wang A, Liu Y. Org. Lett. 2019; 21: 7613 3d Zhu C, Kou L, Bao X. Chin. J. Chem. 2020; 38: 57 3e Tian X, Song L, Rudolph M, Rominger F, Hashmi AS. K. Org. Lett. 2019; 21: 4327 3f Shu C, Wang Y.-H, Zhou B, Li X.-L, Ping Y.-F, Lu X, Ye L.-W. J. Am. Chem. Soc. 2015; 137: 9567 3g Jin H, Huang L, Xie J, Rudolph M, Rominger F, Hashmi AS. K. Angew. Chem. Int. Ed. 2016; 55: 794 For selected examples, see: 4a Vanjari R, Dutta S, Gogoi MP, Gandon V, Sahoo AK. Org. Lett. 2018; 20: 8077 4b Rode ND, Arcadi A, Nicola AD, Marinelli F, Michelet V. Org. Lett. 2018; 20: 5103 4c Jin H, Tian B, Song X, Xie J, Rudolph M, Rominger F, Hashmi AS. K. Angew. Chem. Int. Ed. 2016; 55: 12688 4d Oh KH, Kim JG, Park JK. Org. Lett. 2017; 19: 3994 4e Wezeman T, Zhong S, Nieger M, Bräse S. Angew. Chem. Int. Ed. 2016; 55: 3823 For selected examples, see: 5a Wang Y, Song L.-J, Zhang X, Sun J. Angew. Chem. Int. Ed. 2016; 55: 9704 5b Gati W, Rammah MM, Rammah MB, Couty F, Evano G. J. Am. Chem. Soc. 2012; 134: 9078 5c Xie L.-G, Shaaban S, Chen X, Maulide N. Angew. Chem. Int. Ed. 2016; 55: 12864 5d Garcia P, Evanno Y, George P, Sevrin M, Ricci G, Malacria M, Aubert C, Gandon V. Org. Lett. 2011; 13: 2030 For selected examples, see: 6a Zhu L, Yu Y, Mao Z, Huang X. Org. Lett. 2015; 17: 30 6b Zang W, Wei Y, Shi M. Org. Lett. 2020; 22: 5466 6c Prabagar B, Mallick RK, Prasad R, Gandon V, Sahoo AK. Angew. Chem. Int. Ed. 2019; 58: 2365 6d Dutta S, Mallick RK, Prasad R, Gandon V, Sahoo AK. Angew. Chem. Int. Ed. 2019; 58: 2289 6e Zhou A.-H, He Q, Shu C, Yu Y.-F, Liu S, Zhao T, Zhang W, Lu X, Ye L.-W. Chem. Sci. 2015; 6: 1265 For selected examples, see: 7a Kong Y, Jiang K, Cao J, Fu L, Yu L, Lai G, Cui Y, Hu Z, Wang G. Org. Lett. 2013; 15: 422 7b Okitsu T, Nakata K, Nishigaki K, Michioka N, Karatani M, Wada A. J. Org. Chem. 2014; 79: 5914 7c Oppenheimer J, Johnson WL, Tracey MR, Hsung RP, Yao P.-Y, Liu R, Zhao K. Org. Lett. 2007; 9: 2361 For selected examples, see: 8a Zhang Y, DeKorver KA, Lohse AG, Zhang Y.-S, Huang J, Hsung RP. Org. Lett. 2009; 11: 899 8b Coste A, Couty F, Evano G. Org. Lett. 2009; 11: 4454 8c Kramer S, Dooleweerdt K, Lindhardt AT, Rottländer M, Skrydstrup T. Org. Lett. 2009; 11: 4208 8d Cao Z, Yan S, Zhao C, Sun X, Tian L, Meng X. Tetrahedron 2019; 75: 130534 8e Kim YH, Yoo HJ, Youn SW. Chem. Comm. 2020; 56: 13963 8f Kong Y, Yu L, Cui Y, Cao J. Synthesis 2014; 46: 183 8g Yu L, Deng Y, Cao J. Synthesis 2015; 47: 783 8h Liu D, Nie Q, Zhang R, Cai M. Adv. Synth. Catal. 2018; 360: 3940 8i Hentz A, Retailleau P, Gandon V, Cariou K, Dodd RH. Angew. Chem. Int. Ed. 2014; 53: 8333 8j Nie X.-D, Han X.-L, Sun J.-T, Si C.-M, Wei B.-G, Lin G.-Q. J. Org. Chem. 2021; 86: 3433 8k Chen Z, Nie X.-D, Sun J.-T, Yang A.-M, Wei B.-G. Org. Biomol. Chem. 2021; 19: 2492 For selected examples, see: 9a Compain G, Jouvin K, Martin-Mingot A, Evano G, Marrot J, Thibaudeau S. Chem. Commun. 2012; 48: 5196 9b Plamont R, Graux LV, Clavier H. Eur. J. Org. Chem. 2018; 1372 9c Mulder JA, Kurtz KC. M, Hsung RP, Coverdale H, Frederick MO, Shen L, Zificsak CA. Org. Lett. 2003; 5: 1547 9d Yang Y, Wang L, Zhang F, Zhu G. J. Org. Chem. 2014; 79: 9319 9e Bai Y, Zhang F, Shen J, Luo F, Zhu G. Asian J. Org. Chem. 2015; 4: 626 9f Yang Y, Wang L, Zhang J, Jin Y, Zhu G. Chem. Commun. 2014; 50: 2347 9g Ding R, Li Y, Tao C, Cheng B, Zhai H. Org. Lett. 2015; 17: 3994 9h Xu S, Liu J, Hu D, Bi X. Green Chem. 2015; 17: 184 9i Liu Y.-W, Ma R.-J, Wang Q.-E, Si C.-M, Wei B.-G. Tetrahedron 2020; 76: 131649 9j Dutta S, Yang S, Vanjari R, Mallick RK, Gandon V, Sahoo AK. Angew. Chem. Int. Ed. 2020; 59: 10785 For selected examples, see: 10a Yeh M.-CP, Liang C.-J, Chen H.-F, Weng Y.-T. Adv. Synth. Catal. 2015; 357: 3242 10b Giri SS, Liu R.-S. Adv. Synth. Catal. 2017; 359: 3311 10c Wang X.-N, Winston-McPherson GN, Walton MC, Zhang Y, Hsung RP, DeKorver KA. J. Org. Chem. 2013; 78: 6233 10d Liu H, Yang Y, Wang S, Wu J, Wang X.-N, Chang J. Org. Lett. 2015; 17: 4472 10e Wang H.-R, Huang E.-H, Luo C, Luo W.-F, Xu Y, Qian P.-C, Zhou J.-M, Ye L.-W. Chem. Commun. 2020; 56: 4832 11a Huang L, Arndt M, Gooßen K, Heydt H, Gooßen LJ. Chem. Rev. 2015; 115: 2596 11b Pirnot MT, Wang Y.-M, Buchwald SL. Angew. Chem. Int. Ed. 2016; 55: 48 11c Rabet PT. G, Boyd S, Greaney MF. Angew. Chem. Int. Ed. 2017; 56: 4183 11d Huo J, He G, Chen W, Hu X, Deng Q, Chen D. BMC Chem. 2019; 13: 89 11e Severin R, Doye S. Chem. Soc. Rev. 2007; 36: 1407 11f Kaper T, Fischer M, Thye H, Geik D, Schmidtmann M, Beckhaus R, Doye S. Chem. Eur. J. 2021; 27: 6899 11g Sengupta M, Das S, Islam SM, Bordoloi A. ChemCatChem 2021; 13: 1089 11h Tashrifi Z, Khanaposhtani MM, Biglar M, Larijani B, Mahdavi M. Asian J. Org. Chem. 2020; 9: 969 11i Patel M, Saunthwal RK, Verma AK. Acc. Chem. Res. 2017; 50: 240 12a Guo W, Zhao M, Tan W, Zheng L, Tao K, Fan X. Org. Chem. Front. 2019; 6: 2120 12b Quek JY, Davis TP, Lowe AB. Chem. Soc. Rev. 2013; 42: 7326 12c Rauws TR. M, Maes BU. W. Chem. Soc. Rev. 2012; 41: 2463 13a Liu B, Ning Y, Virelli M, Zanoni G, Anderson EA, Bi X. J. Am. Chem. Soc. 2019; 141: 1593 13b Zhang Z, Huang B, Qiao G, Zhu L, Xiao F, Chen F, Fu B, Zhang Z. Angew. Chem. Int. Ed. 2017; 56: 4320 13c Kim J, Stahl SS. J. Org. Chem. 2015; 80: 2448 13d Zhou M, Li J, Tian C, Sun X, Zhu X, Cheng Y, An G, Li G. J. Org. Chem. 2019; 84: 1015 14a Dong S, Chen J, Qiao K, Fang J, Yang Y, Maron L, Liu B. ACS Catal. 2021; 11: 3790 14b Motolko KS. A, Emslie DJ. H, Jenkins HA. Organometallics 2017; 36: 1601 14c Hayes CE, Platel RH, Schafer LL, Leznoff DB. Organometallics 2012; 31: 6732 14d Manna K, Kruse ML, Sadow AD. ACS Catal. 2011; 1: 1637 15a Gu Q, Wang Q, Dai W, Wang X, Ban Y, Liu T, Zhao Y, Zhang Y, Ling Y, Zeng X. Org. Biomol. Chem. 2021; 19: 2512 15b Zeng X, Wang X, Zhang Y, Zhu L, Zhao Y. Org. Biomol. Chem. 2020; 18: 3734 16 Goulart TA. C, Back DF, Silva SM. E, Zeni G. J. Org. Chem. 2021; 86: 980 Zusatzmaterial Zusatzmaterial Supporting Information (PDF) (opens in new window)
