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-00000083.xml
Download PDF
Synlett 2017; 28(11): 1237-1243
DOI: 10.1055/s-0036-1590202
DOI: 10.1055/s-0036-1590202
synpacts
Copper-Catalyzed Oxidation of Alkanes under Mild Conditions
Further Information
Publication History
Received: 21 January 2017
Accepted after revision: 28 February 2017
Publication Date:
23 March 2017 (online)
Abstract
The selective functionalization of C–H bonds is a critical step in the majority of synthetic organic pathways. Our research lab, among others, takes inspiration from the reactivity of Cu-dependent metalloenzymes to design catalytic systems for the C–H oxidation of challenging substrates (i.e., alkanes). In this Synpacts article, we summarize our recent findings on the Cu-catalyzed peroxidation of C–H bonds with H2O2 under mild conditions.
-
References
- 1 Hartwig JF. J. Am. Chem. Soc. 2016; 138: 2-2
- 2 Brückl T, Baxter RD, Ishihara Y, Baran PS. Acc. Chem. Res. 2012; 45: 826-826
- 3 Newhouse T, Baran PS. Angew. Chem. Int. Ed. 2011; 50: 3362-3362
- 4 Modern Oxidation Methods . Bäckvall J.-E. Wiley-VCH; Weinheim: 2004
- 5 Solomon EI, Heppner DE, Johnston EM, Ginsbach JW, Cirera J, Qayyum M, Kieber-Emmons MT, Kjaergaard CH, Hadt RG, Tian L. Chem. Rev. 2014; 114: 3659-3659
- 6 Costas M, Mehn MP, Jensen MP, Que L. Chem. Rev. 2004; 104: 939-939
- 7 Lewis EA, Tolman WB. Chem. Rev. 2004; 104: 1047-1047
- 8 Mirica LM, Ottenwaelder X, Stack TD. P. Chem. Rev. 2004; 104: 1013-1013
- 9 Lawton TJ, Rosenzweig AC. J. Am. Chem. Soc. 2016; 138: 9327-9327
- 10 Culpepper MA, Cutsail GE, Hoffman BM, Rosenzweig AC. J. Am. Chem. Soc. 2012; 134: 7640-7640
- 11 Beeson WT, Phillips CM, Cate JH. D, Marletta MA. J. Am. Chem. Soc. 2012; 134: 890-890
- 12 Quinlan RJ, Sweeney MD, Lo Leggio L, Otten H, Poulsen J.-CN, Johansen KS, Krogh KB. R. M, Jørgensen CI, Tovborg M, Anthonsen A, Tryfona T, Walter CP, Dupree P, Xu F, Davies GJ, Walton PH. Proc. Natl. Acad. Sci. U.S.A. 2011; 108: 15079-15079
- 13 Klinman JP. J. Biol. Chem. 2006; 281: 3013-3013
- 14 Liu JJ, Diaz DE, Quist DA, Karlin KD. Isr. J. Chem. 2016; 56: 738-738
- 15 Himes RA, Karlin KD. Curr. Opin. Chem. Biol. 2009; 13: 119-119
- 16 Rolff M, Schottenheim J, Decker H, Tuczek F. Chem. Soc. Rev. 2011; 40: 4077-4077
- 17 Chen MS, White MC. Science 2010; 327: 566-566
- 18 Gomez L, Garcia-Bosch I, Company A, Benet-Buchholz J, Polo A, Sala X, Ribas X, Costas M. Angew. Chem. Int. Ed. 2009; 48: 5720-5720
- 19 Chen MS, White MC. Science 2007; 318: 783-783
- 20 Cussó O, Cianfanelli M, Ribas X, Klein Gebbink RJ. M, Costas M. J. Am. Chem. Soc. 2016; 138: 2732-2732
- 21 Allen SE, Walvoord R, Padilla-Salinas R, Kozlowski MC. Chem. Rev. 2013; 113: 6234-6234
- 22 Gephart RT, Warren TH. Organometallics 2012; 31: 7728-7728
- 23 Sambiagio C, Marsden SP, Blacker AJ, McGowan PC. Chem. Soc. Rev. 2014; 43: 3525-3525
- 24 Kirillov AM, Kopylovich MN, Kirillova MV, Haukka M, Silva MF. C. G. d, Pombeiro AJ. L. Angew. Chem. Int. Ed. 2005; 44: 4345-4345
- 25 Barton DH. R, Beviere SD, Chavasiri W, Csuhai E, Doller D. Tetrahedron 1992; 48: 2895-2895
- 26 Sobkowiak A, Qui A, Liu X, Llobet A, Sawyer DT. J. Am. Chem. Soc. 1993; 115: 609-609
- 27 Kirillov AM, Kirillova MV, Pombeiro AJ. L. Coord. Chem. Rev.. 2012; 256: 2741-2741
- 28 Kirillov AM, Kopylovich MN, Kirillova MV, Karabach EY, Haukka M, da Silva MF. C. G, Pombeiro AJ. L. Adv. Synth. Catal. 2006; 348: 159-159
- 29 Conde A, Vilella L, Balcells D, Díaz-Requejo MM, Lledós A, Pérez PJ. J. Am. Chem. Soc. 2013; 135: 3887-3887
- 30 Garcia-Bosch I, Siegler MA. Angew. Chem. Int. Ed. 2016; 55: 12873-12873
- 31 Shul’pin GB. J. Mol. Catal. A: Chem. 2002; 189: 39-39
- 32 Adams AM, Du Bois J, Malik HA. Org. Lett. 2015; 17: 6066-6066
- 33 Shilov AE, Shul’pin GB. Chem. Rev. 1997; 97: 2879-2879
- 34 Sawyer DT, Sobkowiak A, Matsushita T. Acc. Chem. Res. 1996; 29: 409-409
- 35 Oloo WN, Que L. Acc. Chem. Res. 2015; 48: 2612-2612
- 36 Shul’pin GB, Mishra GS, Shul’pina LS, Strelkova TV, Pombeiro AJ. L. Catal. Commun. 2007; 8: 1516-1516
- 37 Slaughter LM, Collman JP, Eberspacher TA, Brauman JI. Inorg. Chem. 2004; 43: 5198-5198
- 38 Prat I, Mathieson JS, Güell M, Ribas X, Luis JM, Cronin L, Costas M. Nat. Chem. 2011; 3: 788-788
- 39 Marusawa H, Ichikawa K, Narita N, Murakami H, Ito K, Tezuka T. Bioorg. Med. Chem. 2002; 10: 2283-2283
- 40 Yamada M, Karlin KD, Fukuzumi S. Chem. Sci. 2016; 7: 2856-2856
- 41 Musser MT. In Ullmann’s Encyclopedia of Industrial Chemistry. Wiley-VCH; Weinheim: 2000