Synthesis 2019; 51(04): 889-898
DOI: 10.1055/s-0037-1610668
paper
© Georg Thieme Verlag Stuttgart · New York

Metal-Free Blue-Light-Mediated Cyclopropanation of Indoles by Aryl(diazo)acetates

Xing Zhang
,
Cong Du
,
He Zhang
,
Xiao-Cai Li
,
Yun-Long Wang
,
,
Mao-Ping Song*
This work was supported by the National Natural Science Foundation of China (Nos. 21772179, 21502173, 21672192) and the Outstanding Young Talent Research Fund of Zhengzhou University (No. 1521316002).
Weitere Informationen

Publikationsverlauf

Received: 12. September 2018

Accepted after revision: 10. Oktober 2018

Publikationsdatum:
20. November 2018 (online)


Abstract

Blue-light-mediated cyclopropanation of indoles with aryl(diazo)acetates has been developed. The salient features of this strategy are that it is metal-free, operationally simple and atom-efficient, and that it uses an environmentally friendly energy source. In this protocol, blue light was employed as the sole energy source for the transformation. A variety of cyclopropane-fused indoline compounds was obtained in moderate to excellent yields and high diastereoselectivities under mild conditions.

Supporting Information

 
  • References

    • 1a Ebner C, Carreira EM. Chem. Rev. 2017; 117: 1165
    • 1b Jin S, Gong J, Qin Y. Angew. Chem. Int. Ed. 2015; 54: 2228
    • 1c Kirillova MS, Muratore ME, Dorel R, Echavarren AM. J. Am. Chem. Soc. 2016; 138: 3671
    • 1d Leng L, Zhou X, Liao Q, Wang F, Song H, Zhang D, Liu XY, Qin Y. Angew. Chem. Int. Ed. 2017; 56: 3703
    • 1e Yang J, Song H, Xiao X, Wang J, Qin Y. Org. Lett. 2006; 8: 2187
    • 1f Zhang D, Song H, Qin Y. Acc. Chem. Res. 2011; 44: 447
    • 2a Ferrer C, Escribano-Cuesta A, Echavarren AM. Tetrahedron 2009; 65: 9015
    • 2b Kam T.-S, Lim K.-H, Yoganathan K, Hayashi M, Komiyama K. Tetrahedron 2004; 60: 10739
    • 3a Huang HX, Jin SJ, Gong J, Zhang D, Song H, Qin Y. Chem. Eur. J. 2015; 21: 13284
    • 3b Shen L, Zhang M, Wu Y, Qin Y. Angew. Chem. Int. Ed. 2008; 47: 3618
    • 3c Gagnon D, Spino C. J. Org. Chem. 2009; 74: 6035

      For selective examples of cyclopropanation of indoles with diazo compounds, see:
    • 4a Davies HL. M, Hedley SJ. Chem. Soc. Rev. 2007; 36: 1109
    • 4b Zhang B, Wee AG. H. Chem. Commun. 2008; 39: 4837
    • 4c Fraile JM, Le Jeune K, Mayoral JA, Ravasio N, Zaccheria F. Org. Biomol. Chem. 2013; 11: 4327
    • 4d Liu K, Xu G, Sun J. Chem. Sci. 2018; 9: 634
    • 4e Zhang B, Wee AG. Org. Biomol. Chem. 2012; 10: 4597
  • 5 For selective examples of cyclopropanation of indoles with N-tosylhydrazones, see: Reddy AR, Hao F, Wu K, Zhou CY, Che CM. Angew. Chem. Int. Ed. 2016; 55: 1810
  • 6 Xu H, Li YP, Cai Y, Wang GP, Zhu SF, Zhou QL. J. Am. Chem. Soc. 2017; 139: 7697
  • 7 Pirovano V, Brambilla E, Tseberlidis G. Org. Lett. 2018; 20: 405
  • 8 Chen W, Ji D.-S, Luo Y.-C, Wang Z.-Y, Xu P.-F. Org. Chem. Front. 2018; 5: 1768

    • For selective visible-light-induced functionalization, see:
    • 9a Liang Y, Zhang X, MacMillan DW. C. Nature 2018; 559: 83
    • 9b Le C, Chen TQ, Liang T, Zhang P, MacMillan DW. C. Science 2018; 360: 1010
    • 9c Gandeepan P, Mo J, Ackermann L. Chem. Commun. 2017; 53: 5906
    • 9d Hari DP, Schroll P, Konig B. J. Am. Chem. Soc. 2012; 134: 2958
    • 9e Mateos J, Cherubini-Celli A, Carofiglio T, Bonchio M, Marino N, Companyo X, Dell’Amico L. Chem. Commun. 2018; 54: 6820
    • 9f Pagire SK, Hossain A, Traub L, Kerres S, Reiser O. Chem. Commun. 2017; 53: 12072
    • 9g Shen ZC, Yang P, Tang Y. J. Org. Chem. 2016; 81: 309
    • 9h Tang X, Studer A. Angew. Chem. Int. Ed. 2018; 57: 814
    • 9i Xiao T, Li L, Lin G, Mao ZW, Zhou L. Org. Lett. 2014; 16: 4232
    • 9j Yang JC, Zhang JY, Zhang JJ, Duan XH, Guo LN. J. Org. Chem. 2018; 83: 1598
    • 9k Zhao YN, Luo YC, Wang ZY, Xu PF. Chem. Commun. 2018; 54: 3993
    • 9l Ye C, Zhang Y, Ding A, Hu Y, Guo H. Sci. Rep. 2018; 8: 2205
    • 9m Li H, Jin R, Li Y, Ding A, Hao X, Guo H. Sci. Rep. 2017; 7: 16559
    • 9n Zhu M, Zhou K, Zhang X, You S.-L. Org. Lett. 2018; 20: 4379
    • 9o Cheng Y.-Z, Zhou K, Li L.-A.-C, Zhang X, You S.-L. Chem. Eur. J. 2018; 24: 12519
    • 9p Liu Y.-Y, Yu X.-Y, Chen J.-R, Qiao M.-M, Qi X, Shi D.-Q, Xiao W.-J. Angew. Chem. Int. Ed. 2017; 56: 9527
    • 9q Xia X.-D, Ren Y.-L, Chen J.-R, Yu X.-L, Lu L.-Q, Zou Y.-Q, Wan J, Xiao W.-J. Chem. Asian J. 2014; 9: 1
    • 10a Strieth-Kalthoff F, James MJ, Teders M, Pitzer L, Glorius F. Chem. Soc. Rev. 2018; 47, 7190
    • 10b Xuan J, Xiao WJ. Angew. Chem. Int. Ed. 2012; 51: 6828
    • 10c Romero NA, Nicewicz DA. Chem. Rev. 2016; 116: 10075
    • 10d Prier CK, Rankic DA, MacMillan DW. C. Chem. Rev. 2013; 113: 5322

      For selective metal- and photocatalyst-free functionalization see:
    • 11a Jurberg ID, Davies HM. L. Chem. Sci. 2018; 9: 5112
    • 11b Li J, Zhang P, Jiang M, Yang H, Zhao Y, Fu H. Org. Lett. 2017; 19: 1994
    • 11c Xiao T, Mei M, He Y, Zhou L. Chem. Commun. 2018; 54: 8865
    • 11d Ni K, Meng LG, Wang K, Wang L. Org. Lett. 2018; 20: 2245
    • 11e Li X, Gu X, Li L, Li P. ACS Catal. 2014; 4: 1897
  • 12 CCDC 1862501 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Centre via www.ccdc.cam.ac.uk/getstructures.
    • 13a Zhu Z, Bally T, Stracener LL, McMahon RJ. J. Am. Chem. Soc. 1999; 121: 2863
    • 13b Wang Y, Yuzawa T, Hamaguchi H.-O, Toscano JP. J. Am. Chem. Soc. 1999; 121: 2875
    • 13c Li YZ, Schuster GB. J. Org. Chem. 1987; 52: 4460
  • 14 Stuart DR, Villemure E, Fagnou K. J. Am. Chem. Soc. 2007; 129: 12072
    • 15a Keipour H, Jalba A, Delage-Laurin A, Ollevier T. J. Org. Chem. 2017; 82: 3000
    • 15b Song Z, Wu Y, Xin T, Jin J, Wen X, Sun H, Xu QL. Chem. Commun. 2016; 52: 6079