Synthesis 2019; 51(17): 3320-3326
DOI: 10.1055/s-0037-1611832
paper
© Georg Thieme Verlag Stuttgart · New York

Cobalt-Catalyzed Cycloisomerization of N,N-Diallylanilines

Jun Liu
a   State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: chenning@mail.buct.edu.cn   Email: jxxu@mail.buct.edu.cn
b   Sinopec Beijing Research Institute of Chemical Industry Yanshan Branch, Beijing 102500, P. R. of China
,
a   State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: chenning@mail.buct.edu.cn   Email: jxxu@mail.buct.edu.cn
,
Minfang Zheng
b   Sinopec Beijing Research Institute of Chemical Industry Yanshan Branch, Beijing 102500, P. R. of China
,
Hongfei Wu
b   Sinopec Beijing Research Institute of Chemical Industry Yanshan Branch, Beijing 102500, P. R. of China
,
Ning Chen  *
a   State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: chenning@mail.buct.edu.cn   Email: jxxu@mail.buct.edu.cn
,
Jiaxi Xu*
a   State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. of China   Email: chenning@mail.buct.edu.cn   Email: jxxu@mail.buct.edu.cn
› Author Affiliations
This work was supported partially from the National Natural Science Foundation of China (No. 21702014 and 21572017) and the Fundamental Research Funds for the Central Universities (XK1802-6).
Further Information

Publication History

Received: 01 March 2019

Accepted after revision: 24 April 2019

Publication Date:
09 May 2019 (online)


Abstract

Cobalt catalysts bearing 2-imino-1,10-phenanthroline ligands are quite efficient bench-stable catalysts for the oligomerization of ethylenes. Herein, their further application was developed in the catalytic transformation of N,N-diallylanilines to pyrrolidines through a cycloisomerization process. In this protocol, chlorobenzene is a vital additive to promote reaction efficiency.

Supporting Information

 
  • References

    • 2a Yamamoto Y. Chem. Rev. 2012; 112: 4736
    • 2b Lloyd-Jones GC. Org. Biomol. Chem. 2013; 1: 215
    • 2c Chen JH, Guo J, Lu Z. Chin. J. Chem. 2018; 36: 1075
    • 3a Yamamoto Y, Nakagai Y, Ohkoshi N, Itoh K. J. Am. Chem. Soc. 2001; 123: 6372
    • 3b Oezdemir I, Cetinkaya E, Cetinkaya B, Cicek M, Semeril D, Bruneau C, Dixneuf PH. Eur. J. Inorg. Chem. 2004; 418
    • 3c Terada Y, Arisawa M, Nishida A. Angew. Chem. Int. Ed. 2004; 43: 4063
    • 3d Fairlamb IJ. S, McGlacken GP, Weissberger F. Chem. Commun. 2006; 988
    • 3e Hong SH, Grubbs RH. J. Am. Chem. Soc. 2006; 128: 3508
    • 3f Miao X, Feder-Kubis J, Fischmeister C, Pernak J, Dixneuf PH. Tetrahedron 2008; 64: 3687
    • 3g Lexer C, Burtscher D, Perner B, Tzur E, Lemcoff NG, Slugovc C. J. Organomet. Chem. 2011; 696: 2466
    • 3h Mallagaray A, Mohammadiannejad-Abbasabadi K, Medina S, Dominguez G, Perez-Castells J. Org. Biomol. Chem. 2012; 10: 6665
    • 3i Mukherjee N, Gawin R, Czarnocki SJ, Gajda R, Malinska M, Wozniak K, Kajetanowicz A, Grela K. J. Organomet. Chem. 2018; 867: 359

      Rh:
    • 4a Bright A, Malone JF, Nicholson JK, Powell J, Shaw BL. J. Chem. Soc., Chem. Commun. 1971; 712
    • 4b Grigg R, Mitchell TR. B, Ramasubbu A. J. Chem. Soc., Chem. Commun. 1980; 27
    • 4c Park J.-W, Chen Z, Dong VM. J. Am. Chem. Soc. 2016; 138: 3310

      Pd:
    • 5a Michelet V, Galland J.-C, Charruault L, Savignac M, Genet J.-P. Org. Lett. 2001; 3: 2065
    • 5b Song Y.-J, Jung IG, Lee H, Lee YT, Chung YK, Jang H.-Y. Tetrahedron Lett. 2007; 48: 6142
    • 5c Mekareeya A, Walker PR, Couce-Rios A, Campbell CD, Steven A, Paton RS, Anderson EA. J. Am. Chem. Soc. 2017; 139: 10104
  • 6 Ti: Okamoto S, Livinghouse T. J. Am. Chem. Soc. 2000; 122: 1223

    • Ni:
    • 7a Necas D, Tursky M, Tislerova I, Kotora M. New J. Chem. 2006; 30: 671
    • 7b Necas D, Ramella D, Rudovsk I, Kotora M. J. Mol. Catal. A: Chem. 2007; 274: 78
    • 7c Ho C.-Y, He L. J. Org. Chem. 2014; 79: 11873
    • 7d Biswas S, Zhang A, Raya B, RajanBabu TV. Adv. Synth. Catal. 2014; 356: 2281
    • 7e Hong X, Wang J, Yang Y.-F, He L, Ho C.-Y, Houk KN. ACS Catal. 2015; 5: 5545
    • 7f Diccianni JB, Heitmann T, Diao T. J. Org. Chem. 2017; 82: 6895
    • 7g Kuang Y, Anthony D, Katigbak J, Marrucci F, Humagain S, Diao T. Chemistry 2017; 3: 268
  • 8 Fe: Darmon JM, Yu RP, Semproni SP, Turner ZR, Stieber SC. E, DeBeer S, Chirik PJ. Organometallics 2014; 33: 5423
    • 9a Schmitz C, Leitner W, Francio G. Chem. Eur. J. 2015; 21: 10696
    • 9b Li K, Li M.-L, Zhang Q, Zhu S.-F, Zhou Q.-L. J. Am. Chem. Soc. 2018; 140: 7458
    • 11a Schmidt VA, Hoyt JM, Margulieux GW, Chirik PJ. J. Am. Chem. Soc. 2015; 137: 7903
    • 11b Docherty JH, Peng J, Dominey AP, Thomas SP. Nat. Chem. 2017; 9: 595
    • 13a Liu J, Zheng M.-F, Li W.-Z, Zhang H.-Y, Wang H.-J, Zhou Y, Li T.-L, Zhao L, Wu H.-F, Xie M.-J, Wu C.-H, Jia Z.-G, Qi Y.-P, Wang J.-L. US Patent 9266982B2, 2016
    • 13b Li T.-L, Zheng M.-F, Liu J, Wang H.-J, Zhang H.-Y, Li W.-Z, Wang J.-L, Piao Y.-L. US Patent 9266983B2, 2016
    • 14a Jie S, Zhang S, Wedeking K, Zhang W, Ma H, Lu X, Deng Y, Sun W.-H. C. R. Chim. 2006; 9: 1500
    • 14b Jie SY, Zhang S, Sun WH, Kuang XF, Liu TF, Guo JP. J. Mol. Catal. A: Chem. 2007; 269: 85
    • 14c Zhang M, Zhang W, Xiao T, Xiang J.-F, Hao X, Sun W.-H. J. Mol. Catal. A: Chem. 2010; 320: 92
  • 15 Yang S.-C, Hsu Y.-C, Gan K.-H. Tetrahedron 2006; 62: 3949