Synthesis, Table of Contents Synthesis 2021; 53(04): 611-622DOI: 10.1055/s-0040-1705947 short review Recent Advances in the Tandem Cyclization/Cycloaddition of Allene Intermediates from Copper-Catalyzed Cross-Coupling of Diazo Compounds with Terminal Alkynes Nuan Chen , Min He , Ting Zhou , Yuqi Zhu , Hong Zhang , Shiyong Peng ∗Recommend Article Abstract Buy Article All articles of this category Abstract This short review summarizes the most recent developments (since 2010) in the tandem cyclization/cycloaddition of allene intermediates, generated from the copper-catalyzed cross-coupling of diazo compounds with terminal alkynes, to afford cyclic compounds. 1 Introduction 2 Cyclization 2.1 Cyclization with Nucleophiles 2.2 Cyclization with Electrophiles 2.3 6π-Electrocyclization 2.4 Other Cyclization 3 Cycloaddition 4 Conclusion Key words Key wordscopper catalysis - diazo compound - terminal alkyne - allene intermediate - cyclization - cycloaddition Full Text References References For selected reviews, see: 1a Ye T, McKervey MA. Chem. Rev. 1994; 94: 1091 1b Padwa A, Austin DJ. Angew. Chem. Int. Ed. 1994; 33: 1797 1c Doyle MP, Forbes DC. Chem. Rev. 1998; 98: 911 1d Zhang Z, Wang J. Tetrahedron 2008; 64: 6577 1e Korneev SM. Eur. J. Org. Chem. 2011; 6153 1f Ford A, Miel H, Ring A, Slattery CN, Maguire AR, McKervey MA. Chem. Rev. 2015; 115: 9981 For typical reviews, see: 2a Zhao X, Zhang Y, Wang J. Chem. Commun. 2012; 48: 10162 2b Che J, Xing D, Hu W. Curr. Org. Chem. 2016; 20: 41 2c Torres Ò, Pla-Quintana A. Tetrahedron Lett. 2016; 57: 3881 3 For a typical review, see: Xiao Q, Zhang Y, Wang J. Acc. Chem. Res. 2013; 46: 236 4 Suárez A, Fu GC. Angew. Chem. Int. Ed. 2004; 43: 3580 For typical reviews, see: 5a Hossain ML, Wang J. Chem. Rec. 2018; 18: 1548 5b Xia Y, Qiu D, Wang J. Chem. Rev. 2017; 117: 13810 6 Liu H, Feng W, Kee CW, Leow D, Loh W.-T, Tan C.-H. Adv. Synth. Catal. 2010; 352: 3373 7 Kumaraswamy G, Jayaprakash N, Balakishan G. Org. Biomol. Chem. 2011; 9: 7913 8 Zhou L, Shi Y, Xiao Q, Liu Y, Ye F, Zhang Y, Wang J. Org. Lett. 2011; 13: 968 9 Xiao T, Dong X, Zhou L. Org. Biomol. Chem. 2013; 11: 1490 10 Hossain ML, Ye F, Zhang Y, Wang J. Tetrahedron 2014; 70: 6957 11 Liu G, Xu G, Li J, Ding D, Sun J. Org. Biomol. Chem. 2014; 12: 1387 12 Liu K, Zhu C, Min J, Peng S, Xu G, Sun J. Angew. Chem. Int. Ed. 2015; 54: 12962 13 Min J, Xu G, Sun J. Chem. Commun. 2017; 53: 4350 14 Yan S, Cao S, Sun J. Org. Biomol. Chem. 2017; 15: 5272 15 Hossain ML, Wang K, Ye F, Zhang Y, Wang J. Chin. J. Catal. 2017; 38: 115 16 Ji D, Liu K, Sun J. Org. Lett. 2018; 20: 7708 17 Xu S, Chen R, Fu Z, Gao Y, Wang J. J. Org. Chem. 2018; 83: 6186 18 Kumaraswamy G, Balakishan G. Eur. J. Org. Chem. 2015; 3141 19 Min J, Xu G, Sun J. J. Org. Chem. 2017; 82: 5492 20 Heinrich CF, Miesch M, Miesch L. Org. Biomol. Chem. 2015; 13: 2153 21 Ji D, Liu K, Sun J. Org. Lett. 2017; 19: 6440 For leading examples, see: 22a Ye F, Hossain ML, Xu Y, Ma X, Xiao Q, Zhang Y, Wang J. Chem. Asian J. 2013; 8: 1404 22b Wang C, Ye F, Wu C, Zhang Y, Wang J. J. Org. Chem. 2015; 80: 8748 22c Zhang Z, Zhou Q, Yu W, Li T, Wu G, Zhang Y, Wang J. Org. Lett. 2015; 17: 2474 22d Wu C, Liu Z, Zhang Z, Ye F, Deng G, Zhang Y, Wang J. Adv. Synth. Catal. 2016; 358: 2480 22e Zhou Y, Ye F, Zhou Q, Zhang Y, Wang J. Org. Lett. 2016; 18: 2024 23 Lv X, Kang Z, Xing D, Hu W. Org. Lett. 2018; 20: 4843 24 Wang Y, Burton DJ. Org. Lett. 2006; 8: 5295 25 Ye F, Shi Y, Zhou L, Xiao Q, Zhang Y, Wang J. Org. Lett. 2011; 13: 5020 26 Hossain ML, Ye F, Liu Z, Xia Y, Shi Y, Zhou L, Zhang Y, Wang J. J. Org. Chem. 2014; 79: 8689 27 Zhu R, Cheng G, Jia C, Xue L, Cui X. J. Org. Chem. 2016; 81: 7539 28 Li P, Yu L, Zhang X, Shi M. Org. Lett. 2018; 20: 4516 29 Luo H, He C, Jiang H, Zhu S. Chin. J. Chem. 2020; 38: 1052 30 Zhou L, Ma J, Zhang Y, Wang J. Tetrahedron Lett. 2011; 52: 5484 31 Mondal S, Nechab M, Campolo D, Vanthuyne N, Bertrand MP. Adv. Synth. Catal. 2012; 354: 1987 32 Zhang H, Cao T, Luo H, Chen L, Zhu S. Org. Chem. Front. 2019; 6: 1118 33 Ma J, Zhang L, Zhu S. Curr. Org. Chem. 2016; 20: 102 For typical reviews, see: 34a Alcaide B, Almendros P, Aragoncillo C. Chem. Soc. Rev. 2010; 39: 783 34b Mascareñas JL, Varela I, López F. Acc. Chem. Res. 2019; 52: 465 35 He M, Chen N, Zhou T, Li Q, Li H, Lang M, Wang J, Peng S. Org. Lett. 2019; 21: 9559 36 For a typical review on bisallene chemistry, see: Alcaide B, Almendros P, Aragoncillo C. Chem. Soc. Rev. 2014; 43: 3106 37 He M, Chen N, Liu L, Zhu Y, Li Q, Li H, Lang M, Wang J, Peng S. J. Org. Chem. 2020; 85: 4418
