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 2018; 50(15): 2915-2923
DOI: 10.1055/s-0037-1610005
DOI: 10.1055/s-0037-1610005
special topic
Quinone C–H Alkylations via Oxidative Radical Processes
We gratefully acknowledge the University of California, Merced for funding. R.D.B acknowledges funding from the University of California, Merced MACES Center, NASA parent.Weitere Informationen
Publikationsverlauf
Received: 01. März 2018
Accepted after revision: 18. April 2018
Publikationsdatum:
06. Juni 2018 (online)
Published as part of the Special Topic Modern Radical Methods and their Strategic Applications in Synthesis
Abstract
A brief survey of radical additions to quinones is reported. Carboxylic acids, aldehydes, and unprotected amino acids are compared as alkyl radical precursors for the mono- or bis- C–H alkylation of several quinones. Two methods for radical initiation are discussed comparing inorganic persulfates and Selectfluor as stoichiometric oxidants. Kinetic analysis reveals dramatic differences in the rate of radical initiation depending on the identity of the radical precursor and oxidant. Synthetic strategies for efficiently producing alkyl-quinones are discussed in the context of selecting optimum radical precursors and initiators depending on quinone identity and functional groups present.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610005.
- Supporting Information
-
References
- 1a Yang T.-K., Shen C.-Y.; 1,4-Benzoquinone, In e-EROS Encyclopedia of Reagents for Organic Synthesis; 2001;
- 1b Buckle D. R., Collier S. J., McLaws M. D.; 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone, In e-EROS Encyclopedia of Reagents for Organic Synthesis; 2005;
- 1c Popp BV. Stahl SS. Organometallic Oxidation Catalysis. In Topics in Organometallic Chemistry. Vol 22. Meyer F. Limberg C. Springer; Berlin: 2006
- 1d Nawrat CC. Moody CJ. Angew. Chem. Int. Ed. 2014; 53: 2056
- 1e Garuti L. Roberti M. Pizzirani D. Mini Rev. Med. Chem. 2007; 7: 481
- 2 Bian J. Li X. Wang N. Wu X. You Q. Zhang X. Eur. J. Med. Chem. 2017; 129: 27
- 3a Hughs W. Leoung G. Kramer F. Bozzette SA. Safrin S. Frame P. Clumeck N. Masur H. Lancaster D. Chan C. Lavelle J. Rosenstock J. Falloon J. Feinberg J. LaFon S. Rogers M. Sattler F. N. Engl. J. Med. 1993; 328: 1521
- 3b Muragur GR. Kiara HK. McHardy N. Vet. Parasitol. 1999; 87: 25
- 3c Shearer MJ. Newman P. Thromb. Haemost. 2008; 100: 530
- 4a Khader M. Eckl PM. Iran J. Basic Med. Sci. 2014; 17: 950
- 4b Breyer S. Effenberger K. Schobert R. ChemMedChem 2009; 4: 761
- 5 Nasiri HR. Madej MG. Panisch R. Lafontaine M. Bats JW. Lancaster CR. D. Schwalbe H. J. Med. Chem. 2013; 56: 9530
- 6a Ge B. Wang D. Dong W. Ma P. Li Y. Ding Y. Tetrahedron Lett. 2014; 55: 5443
- 6b Yu X. Wan H. Xu Z. Xu X. Wang D. RSC Adv. 2016; 6: 62298
- 6c Wang D. Ge B. Li L. Shan J. Ding Y. J. Org. Chem. 2014; 79: 8607
- 6d Walker SE. Jordan-Hore JA. Johnson DG. Macgregor SA. Lee A.-L. Angew. Chem. Int. Ed. 2014; 53: 13876
- 6e Gan X. Jiang W. Wang W. Hu L. Org. Lett. 2009; 11: 589
- 6f Echavarren AM. de Frutos Ó. Tamayo N. Noheda P. Calle P. J. Org. Chem. 1997; 62: 4524
- 6g Xu X.-L. Li Z. Angew. Chem. Int. Ed. 2017; 56: 8196
- 6h Wang D. Ge B. Du L. Miao H. Ding Y. Synlett 2014; 25: 2895
- 7a Fujiwara Y. Domingo V. Seiple IB. Gianatassio R. Del Bel M. Baran PS. J. Am. Chem. Soc. 2011; 133: 3292
- 7b Dixon DD. Lockner JW. Zhou Q. Baran PS. J. Am. Chem. Soc. 2012; 134: 8432
- 7c Wang J. Wang S. Wang G. Zhang J. Yu X.-Q. Chem. Commun. 2012; 48: 11769
- 7d Nasiri HR. Ferner J. Tükek C. Krishnathas R. Schwalbe H. Tetrahedron Lett. 2015; 56: 2231
- 8 Gutiérrez-Bonet Á. Remeur C. Matsui JK. Molander GA. J. Am. Chem. Soc. 2017; 139: 12251
- 9 Mai DN. Baxter RD. Org. Lett. 2016; 18: 3738
- 10a Hua AM. Mai DN. Martinez R. Baxter RD. Org. Lett. 2017; 19: 2949
- 10b Galloway JD. Mai DN. Baxter RD. Org. Lett. 2017; 19: 5772
- 11 Schonberg A. Moubacher R. Chem. Rev. 1952; 50: 261
- 12a Minisci F. Citterio A. Giordano C. Acc. Chem. Res. 1983; 16: 27
- 12b Liang T. Neumann CN. Ritter T. Angew. Chem. Int. Ed. 2013; 52: 8214
- 13 Baxter RD. Liang Y. Hong X. Brown TA. Zare RN. Houk KN. Baran PS. Blackmond DG. ACS Cent. Sci. 2015; 1: 456
- 14 Radical formation is believed to occur via a hydrogen-atom abstraction/decarbonylation sequence rather than an oxidation/decarboxylation sequence. Evidence for this mechanism is provided via the presence of acylated products from aldehydes in reference 9 above.
- 15 Patil CP. Akamanchi GK. RSC Adv. 2014; 4: 58214
- 16 Murahashi S.-I. Miyaguchi N. Noda S. Naota T. Fujii A. Inubushi Y. Komiya N. Eur. J. Org. Chem. 2011; 5355
- 17 Yue Y. Novianti ML. Tessensohn ME. Hirao H. Webster RD. Org. Biomol. Chem. 2015; 13: 11732
- 18 Commandeur C. Chalumeau C. Dessolin J. Laguerre M. Eur. J. Org. Chem. 2007; 18: 3045
- 19 Miyamura H. Shiramizu M. Matsubara R. Kobayashi S. Angew. Chem. Int. Ed. 2008; 47: 8093