RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2024; 56(17): 2655-2662
DOI: 10.1055/a-2331-2707
DOI: 10.1055/a-2331-2707
paper
Special Topic Dedicated to Prof. Erick Carreira
Palladium-Catalyzed Cyanations of Aryl Imidazolylsulfonates with K4[Fe(CN)6]: A Pragmatic Approach to Benzonitriles from Phenols
D.E.F. would like to thank the Max and Minnie Tomerlin Voelcker Fund for unrestricted funds to our laboratories at UTSA. The UTSA NMR and X-ray facilities are supported by the National Science Foundation (NSF) (CHE-1625963 and CHE-1920057).
Dedicated to Prof. Erick M. Carreira on the occasion of his 60th birthday.
Abstract
A general Pd-catalyzed approach for the conversion of phenols into benzonitriles via aryl imidazolylsulfonates with a non-toxic cyanide source, potassium ferrocyanide, has been developed. Salient features of this method include low palladium precatalyst loadings (as low as 1.0 mol% total Pd), mild reaction conditions, and environmentally benign by-products compared to other (pseudo)halide aryl electrophiles. The initial scope of the reaction on a range of phenolic precursors is demonstrated including a one-pot, two-step approach to convert phenols directly into benzonitriles.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2331-2707.
- Supporting Information
Publikationsverlauf
Eingereicht: 11. April 2024
Angenommen nach Revision: 22. Mai 2024
Accepted Manuscript online:
22. Mai 2024
Artikel online veröffentlicht:
18. Juni 2024
© 2024. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1 Gim HJ, Park J, Jung ME, Houk KN. Sci. Rep. 2021; 11: 15887
- 2 Jeanmart S, Edmunds AJ, Lamberth C, Pouliot M. Bioorg. Med. Chem. 2016; 24: 317
- 3 Ge S, Green RA, Hartwig JF. J. Am. Chem. Soc. 2014; 136: 1617
- 4 Mills LR, Edjoc RK, Rousseaux SA. L. J. Am. Chem. Soc. 2021; 143: 10422
- 5 Xia Y, Jiang H, Wu W. Eur. J. Org. Chem. 2021; 6658
- 6 McGuire BA, Burkhardt AM, Kalenskii S, Shingledecker CN, Remijan AJ, Herbst E, McCarthy MC. Science 2018; 359: 202
- 7 Yan G, Zhang Y, Wang J. Adv. Synth. Catal. 2017; 359: 4068
- 8 Neetha M, Afsina CM. A, Aneeja T, Anilkumar G. RSC Adv. 2020; 10: 33683
- 9 Wallace DJ, Campos KR, Shultz CS, Klapars A, Zewge D, Crump BR, Phenix BD, McWilliams JC, Krska S, Sun Y, Chen C.-y, Spindler F. Org. Process Res. Dev. 2009; 13: 84
- 10 Leahy DK, Li J, Sausker JB, Zhu J, Fitzgerald MA, Lai C, Buono FG, Braem A, de Mas N, Manaloto Z, Lo E, Merkl W, Su B.-N, Gao Q, Ng AT, Hartz RA. Org. Process Res. Dev. 2010; 14: 1221
- 11 Buono FG, Chidambaram R, Mueller RH, Waltermire RE. Org. Lett. 2008; 10: 5325
- 12 Coombs JR, Fraunhoffer KJ, Simmons EM, Stevens JM, Wisniewski SR, Yu M. J. Org. Chem. 2017; 82: 7040
- 13 Cohen DT, Buchwald SL. Org. Lett. 2015; 17: 202
- 14 Tschaen DM, Desmond R, King AO, Fortin MC, Pipik B, King S, Verhoeven TR. Synth. Commun. 1994; 24: 887
- 15 Wisniewski SR, Stevens JM, Yu M, Fraunhoffer KJ, Romero EO, Savage SA. J. Org. Chem. 2019; 84: 4704
- 16 Marcantonio KM, Frey LF, Liu Y, Chen Y, Strine J, Phenix B, Wallace DJ, Chen CY. Org. Lett. 2004; 6: 3723
- 17 Dobbs KD, Marshall WJ, Grushin VV. J. Am. Chem. Soc. 2007; 129: 30
- 18 Schareina T, Zapf A, Beller M. Chem. Commun. 2004; 1388
- 19 Nauth AM, Opatz T. Org. Biomol. Chem. 2019; 17: 11
- 20 Weissman SA, Zewge D, Chen C. J. Org. Chem. 2005; 70: 1508
- 21 Hartung J, Wang X, Song ZJ, Chen Y, Guo F, Li Z. Org. Process Res. Dev. 2022; 26: 3161
- 22 Richardson J, Mutton SP. J. Org. Chem. 2018; 83: 4922
- 23 Yeung PY, Tsang CP, Kwong FY. Tetrahedron Lett. 2011; 52: 7038
- 24 Yeung PY, So CM, Lau CP, Kwong FY. Org. Lett. 2011; 13: 648
- 25 Mondal B, Acharyya K, Howlader P, Mukherjee PS. J. Am. Chem. Soc. 2016; 138: 1709
- 26 Yu H, Richey RN, Miller WD, Xu J, May SA. J. Org. Chem. 2011; 76: 665
- 27 Senecal TD, Shu W, Buchwald SL. Angew. Chem. Int. Ed. 2013; 52: 10035
- 28 Zhu Y.-Z, Cai C. Synth. Commun. 2008; 38: 2753
- 29 Yeung PY, So CM, Lau CP, Kwong FY. Angew. Chem. Int. Ed. 2010; 49: 8918
- 30 Sunil K, Rajendra MA, Sajith AM, Joy MN, Bakulev VA, Haridas KR. Synlett 2020; 31: 1629
- 31 Lindstrom AB, Strynar MJ, Libelo EL. Environ. Sci. Technol. 2011; 45: 7954
- 32 Albaneze-Walker J, Raju R, Vance JA, Goodman AJ, Reeder MR, Liao J, Maust MT, Irish PA, Espino P, Andrews DR. Org. Lett. 2009; 11: 1463
- 33 Luo Y, Wu J. Organometallics 2009; 28: 6823
- 34 Ackermann L, Sandmann R, Song W. Org. Lett. 2011; 13: 1784
- 35 Kovacs S, Csincsi AI, Nagy TZ, Boros S, Timari G, Novak Z. Org. Lett. 2012; 14: 2022
- 36 Cívicos JF, Alonso DA, Nájera C. Adv. Synth. Catal. 2013; 355: 203
- 37 DeAngelis AJ, Gildner PG, Chow R, Colacot TJ. J. Org. Chem. 2015; 80: 6794