Synlett 2018; 29(04): 383-387
DOI: 10.1055/s-0036-1591532
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© Georg Thieme Verlag Stuttgart · New York

Iron-Catalyzed Wacker-Type Oxidation

Binbin Liu
a   Jiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No. 1, Nanjing 210023, P. R. of China
,
Wei Han  *
a   Jiangsu Key Laboratory of Biofunctional Materials, Key Laboratory of Applied Photochemistry, School of Chemistry and Materials Science, Nanjing Normal University, Wenyuan Road No. 1, Nanjing 210023, P. R. of China
b   Jiangsu Collaborative Innovation Center of Biomedical Functional Materials, Nanjing 210023, P. R. of China   eMail: hanwei@njnu.edu.cn
› Institutsangaben
This work was sponsored by the Natural Science Foundation of China (21776139, 21302099), the Natural Science Foundation of Jiangsu Province (BK20161553), the Natural Science Foundation of Jiangsu Provincial Colleges and Universities (16KJB150019), the SRF for ROCS, SEM, the Qing Lan project of Nanjing Normal University, and the Priority Academic Program Development of Jiangsu Higher Education Institutions
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Publikationsverlauf

Received: 03. Dezember 2017

Accepted after revision: 27. Dezember 2017

Publikationsdatum:
29. Januar 2018 (online)


Abstract

Compared with the widespread use of Pd-catalyzed Wacker-type oxidation of olefins, iron catalysis for this transformation is almost virgin territory. Our work on an iron-catalyzed Wacker-type oxidation through reductive activation of dioxygen is discussed here. This novel single-electron-transfer process not only addresses the issues of the Pd-catalyzed two-electron Wacker-type oxidation, but also possesses unprecedented functional-group tolerance and chemoselectivity. Importantly, the catalytic system uses ambient air as the sole oxidant, and it permits late-stage oxidations of complex molecules.

 
  • References

    • 1a Smidt J. Hafner W. Jira R. Sedlmeier J. Sieber R. Rüttinger R. Kojer H. Angew. Chem. 1959; 71: 176
    • 1b Smidt J. Hafner W. Jira R. Sieber R. Sedlmeier J. Sabel A. Angew. Chem. 1962; 74: 93
    • 1c Tsuji J. Synthesis 1984; 369
    • 1d Jira R. Angew. Chem. Int. Ed. 2009; 48: 9034
  • 2 Tsuji J. Palladium Reagents and Catalysts: New Perspectives for the 21st Century. Wiley; Chichester: 2004. 2nd ed.
    • 3a Morandi B. Wickens ZK. Grubbs RH. Angew. Chem. Int. Ed. 2013; 52: 2944
    • 3b Lerch MM. Morandi B. Wickens ZK. Grubbs RH. Angew. Chem. Int. Ed. 2014; 53: 8654
    • 3c Morandi B. Wickens ZK. Grubbs RH. Angew. Chem. Int. Ed. 2013; 52: 9751
    • 3d Mitsudome T. Mizumoto K. Mizugaki T. Jitsukawa K. Kaneda K. Angew. Chem. Int. Ed. 2010; 49: 1238
    • 3e Mitsudome T. Yoshida S. Mizugaki T. Jitsukawa K. Kaneda K. Angew. Chem. Int. Ed. 2013; 52: 5961
    • 3f Mitsudome T. Yoshida S. Tsubomoto Y. Mizugaki T. Jitsukawa K. Kaneda K. Tetrahedron Lett. 2013; 54: 1596
    • 3g DeLuca RJ. Edwards JL. Steffens LD. Michel BW. Qiao X. Zhu C. Cook SP. Sigman MS. J. Org. Chem. 2013; 78: 1682
    • 3h Michel BW. Steffens LD. Sigman MS. J. Am. Chem. Soc. 2011; 133: 8317
    • 3i Michel BW. McCombs JR. Winkler A. Sigman MS. Angew. Chem. Int. Ed. 2010; 49: 7312
    • 3j Michel BW. Camelio AM. Cornell CN. Sigman MS. J. Am. Chem. Soc. 2009; 131: 6076
    • 3k McCombs JR. Michel BW. Sigman MS. J. Org. Chem. 2011; 76: 3609
    • 3l Jensen KH. Webb JD. Sigman MS. J. Am. Chem. Soc. 2010; 132: 17471
    • 3m Anderson BJ. Keith JA. Sigman MS. J. Am. Chem. Soc. 2010; 132: 11872
    • 3n Weiner B. Baeza A. Jerphagnon T. Feringa BL. J. Am. Chem. Soc. 2009; 131: 9473
    • 4a Baiju TV. Gravel E. Doris E. Namboothiri IN. N. Tetrahedron Lett. 2016; 57: 3993
    • 4b Alandis N. Rico-Lattes I. Lattes A. New J. Chem. 1994; 18: 1147
    • 4c Sommovigo M. Alper H. J. Mol. Catal. 1994; 88: 151
    • 4d Barak G. Sasson Y. J. Chem. Soc., Chem. Commun. 1987; 1266
    • 5a Sigman MS. Werner EW. Acc. Chem. Res. 2012; 45: 874
    • 5b Cao Q. Bailie DS. Fu R. Muldoon MJ. Green Chem. 2015; 17: 2750
    • 5c Wang X. Venkataramanan NS. Kawanami H. Ikushima Y. Green Chem. 2007; 9: 1352
  • 6 Stahl SS. Science 2005; 309: 1824
  • 7 Zhang G. Hu X. Chiang C.-W. Yi H. Pei P. Singh AK. Lei A. J. Am. Chem. Soc. 2016; 138: 12037
    • 8a Plietker B. Iron Catalysis in Organic Chemistry . Wiley-VCH; Weinheim: 2008
    • 8b Bolm C. Legros J. Le Paih JL. Zani L. Chem. Rev. 2004; 104: 6217
    • 8c Enthaler S. Junge K. Beller M. Angew. Chem. Int. Ed. 2008; 47: 3317
    • 8d Bauer I. Knölker H.-J. Chem. Rev. 2015; 115: 3170
    • 8e Sun C.-L. Li B.-J. Shi Z.-J. Chem. Rev. 2011; 111: 1293
  • 9 Chen G.-Q. Xu Z.-J. Zhou C.-Y. Che C.-M. Chem. Commun. 2011; 47: 10963
  • 10 Chowdhury AD. Ray R. Lahiri GK. Chem. Commun. 2012; 48: 5497
  • 11 Du Y.-D. Tse C.-W. Xu Z.-J. Liu Y. Che C.-M. Chem. Commun. 2014; 50: 12669
  • 12 Meunier B. de Visser SP. Shaik S. Chem. Rev. 2004; 104: 3947
    • 13a Crossley SW. M. Obradors C. Martinez RM. Shenvi RA. Chem. Rev. 2016; 116: 8912
    • 13b Hashimoto T. Hirose D. Taniguchi T. Angew. Chem. Int. Ed. 2014; 53: 2730
    • 13c Leggans EK. Barker TJ. Duncan KK. Boger DL. Org. Lett. 2012; 14: 1428
    • 13d Taniguchi T. Goto N. Nishibata A. Ishibashi H. Org. Lett. 2010; 12: 112
    • 13e Sugimori T. Horike S.-i. Tsumura S. Handa M. Kasuga K. Inorg. Chim. Acta 1998; 283: 275
    • 13f Takeuchi M. Kodera M. Kano K. Yoshida Z.-i. J. Mol. Catal. A: Chem. 1996; 113: 51
    • 14a Gui J. Pan C.-M. Jin Y. Qin T. Lo JC. Lee BJ. Spergel SH. Mertzman ME. Pitts WJ. La Cruz TE. Schmidt MA. Darvatkar N. Natarajan SR. Baran PS. Science 2015; 348: 886
    • 14b Lo JC. Gui J. Yabe Y. Pan C.-M. Baran PS. Nature 2014; 516: 343
    • 14c Lo JC. Kim DY. Pan C.-M. Edwards JT. Yabe Y. Gui J. Qin T. Gutiérrez S. Giacoboni J. Smith MW. Holland PL. Baran PS. J. Am. Chem. Soc. 2017; 139: 2484
    • 14d Lo JC. Yabe Y. Baran PS. J. Am. Chem. Soc. 2014; 136: 1304
    • 14e Dao HT. Li C. Michaudel Q. Maxwell BD. Baran PS. J. Am. Chem. Soc. 2015; 137: 8046
  • 15 Liu B. Jin F. Wang T. Yuan X. Han W. Angew. Chem. Int. Ed. 2017; 56: 12712