Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2021; 53(21): 4068-4074
DOI: 10.1055/a-1534-0624
DOI: 10.1055/a-1534-0624
paper
Cobalt-Catalyzed Preparation of N-Heterocyclic Organozinc Reagents from the Corresponding Heteroaryl Chlorides
We thank the Ludwig-Maximilians University Munich and Syngenta AG (Stein, Switzerland) for financial support.
Abstract
Various substituted and unsubstituted N-heteroaryl chlorides have been converted into their corresponding organozinc species using zinc dust in the presence of zinc pivalate and 10% CoCl2 in benzonitrile at 25 °C. The resulting heteroarylzinc reagents were obtained in 43–98% yield within 9–48 h and reacted with a broad range of electrophiles, leading to the functionalized heteroarenes.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1534-0624.
- Supporting Information
Publication History
Received: 08 June 2021
Accepted after revision: 22 June 2021
Accepted Manuscript online:
22 June 2021
Article published online:
29 July 2021
© 2021. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Dinesh K, Kumar JS. Curr. Med. Chem. 2016; 23: 4338
- 1b Taylor AP, Robinson RP, Fobian YM, Blakemore DC, Jones LH, Fadeyi O. Org. Biomol. Chem. 2016; 14: 6611
- 1c Martins P, Jesus J, Santos S, Raposo LR, Roma-Rodrigues C, Baptista PV, Fernandes AR. Molecules 2015; 20: 16852
- 1d Chen D, Su S.-J, Cao Y. J. Mater. Chem. C 2014; 2: 9565
- 1e Meanwell NA. J. Med. Chem. 2011; 54: 2529
- 1f Baxter PN. W, Dali-Youcef R. J. Org. Chem. 2005; 70: 4935
- 1g Li X.-Q, Andersson TB, Ahlstrøm M, Weidolf L. Drug Metab. Dispos. 2004; 32: 821
- 1h Anttila SA. K, Leinonen EV. J. CNS Drug Rev. 2001; 7: 249
- 2a Vitaku E, Smith DT, Njardarson JT. J. Med. Chem. 2014; 57: 10257
- 2b Taylor RD, MacCoss M, Lawson AD. G. J. Med. Chem. 2014; 57: 5845
- 3a Tüllmann CP, Steiner S, Knochel P. Synthesis 2020; 52: 2357
- 3b Ziegler DS, Klier L, Müller N, Karaghiosoff K, Knochel P. Synthesis 2018; 50: 4383
- 3c Levin VV, Agababyan DP, Struchkova MI, Dilman AD. Synthesis 2018; 50: 2930
- 3d Castelló-Micó A, Knochel P. Synthesis 2018; 50: 155
- 3e Benischke AD, Ellwart M, Becker MR, Knochel P. Synthesis 2016; 48: 1101
- 3f Dagousset G, François C, León T, Blanc R, Sansiaume-Dagousset E, Knochel P. Synthesis 2014; 46: 3133
- 3g Knochel P, Millot N, Rodriguez AL. In Organic Reactions, Vol. 58. Wiley-VCH; Weinheim: 2004: 417-759
- 3h Knochel P, Singer RD. Chem. Rev. 1993; 93: 2117
- 4a Benischke AD, Le Corre G, Knochel P. Chem. Eur. J. 2017; 23: 778
- 4b Boudet N, Sase S, Sinha P, Liu C.-Y, Krasovskiy A, Knochel P. J. Am. Chem. Soc. 2007; 129: 12358
- 4c Piller FM, Metzger A, Schade MA, Haag BA, Gavryushin A, Knochel P. Chem. Eur. J. 2009; 15: 7192
- 4d Metzger A, Argyo C, Knochel P. Synthesis 2010; 882
- 4e Metzger A, Schade MA, Knochel P. Org. Lett. 2008; 10: 1107
- 4f Krasovskiy A, Malakhov V, Gavryushin A, Knochel P. Angew. Chem. Int. Ed. 2006; 45: 6040
- 4g Zhu L, Wehmeyer RM, Rieke RD. J. Org. Chem. 1991; 56: 1445
- 4h Rieke RD. Science 1989; 246: 1260
- 4i Burns TP, Rieke RD. J. Org. Chem. 1983; 48: 4141
- 6 Knochel P. Handbook of Functionalized Organometallics, Vol. 1 and 2. Wiley-VCH; Weinheim: 2005
- 7a Kazmierski I, Gosmini C, Paris J.-M, Périchon J. Synlett 2006; 881
- 7b Gosmini C, Amatore M, Claudel S, Périchon J. Synlett 2005; 2171
- 7c Kazmierski I, Gosmini C, Paris J.-M, Périchon J. Tetrahedron Lett. 2003; 44: 6417
- 7d Fillon H, Gosmini C, Périchon J. J. Am. Chem. Soc. 2003; 125: 3867
- 8 M.-Y Jin, Yoshikai N. J. Org. Chem. 2011; 76: 1972
- 9 Piller FM, Appukkuttan P, Gavryushin A, Helm M, Knochel P. Angew. Chem. Int. Ed. 2008; 47: 6802
- 10a Polleux L, Labbé E, Buriez O, Périchon J. Chem. Eur. J. 2005; 11: 4678
- 10b Seka S, Buriez O, Périchon J. Chem. Eur. J. 2003; 9: 3597
- 11 For a more detailed screening, see the Supporting Information.
- 12 Farina V. e-EROS: Encyclopedia for Reagents in Organic Synthesis 2002;
- 13a Balkenhohl M, Jangra H, Lenz T, Ebeling M, Zipse H, Karaghiosoff K, Knochel P. Angew. Chem. Int. Ed. 2019; 58: 9244
- 13b Abou-Hamdan H, Désaubry L. J. Org. Chem. 2018; 83: 2954
- 13c Asif M. Curr. Med. Chem. 2012; 19: 2984
- 13d Perio A, Chambon JP, Calassi R, Heaulme M, Biziere K. J. Pharmacol. Exp. Ther. 1986; 239: 542
- 14 Vlad G, Horvath IT. J. Org. Chem. 2002; 67: 6550
- 15 Zheng X, Song B, Xu B. Eur. J. Org. Chem. 2010; 4376
- 16 Metzger A, Melzig L, Despotopoulou C, Knochel P. Org. Lett. 2009; 11: 4228
- 17 Melzig L, Metzger A, Knochel P. Chem. Eur. J. 2011; 17: 2948
- 18 Lin X, Hou C, Li H, Weng Z. Chem. Eur. J. 2016; 22: 2075