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 2017; 49(11): 2423-2434
DOI: 10.1055/s-0036-1588162
DOI: 10.1055/s-0036-1588162
paper
Copper Acetate Mediated α-Oxysulfonylation of α-Diazo β-Ketosulfones
Further Information
Publication History
Received: 28 December 2016
Accepted after revision: 07 March 2017
Publication Date:
30 March 2017 (online)
Abstract
Copper acetate mediated α-oxysulfonylation of α-diazo β-ketosulfones in wet nitromethane under nitrogen provides α-oxysulfonyl β-ketosulfones. The use of different copper salts is investigated for the development of a facile and efficient transformation. A plausible mechanism is proposed herein.
Supporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588162.
- Supporting Information
- CIF File
-
References
- 1a For C–X bond formation, see: Luh T.-Y. Leung M.-k. Wong K.-T. Chem. Rev. 2000; 100: 3187
- 1b For C–O bond formation, see: Kumar R. Wirth T. Top. Curr. Chem. 2016; 373: 243
- 1c Beccalli EM. Broggini G. Martinelli M. Sottocornola S. Chem. Rev. 2007; 107: 5318
- 1d Mailyan AK. Eickhoff JA. Minakova AS. Gu Z. Lu P. Zakarian A. Chem. Rev. 2016; 116: 4441
- 1e For C–S bond formation, see: Beletskaya IP. Ananikov VP. Chem. Rev. 2011; 111: 1596
- 1f For C–B bond formation, see: Mkhalid IA. I. Barnard JH. Marder TB. Murphy JM. Hartwig JF. Chem. Rev. 2010; 110: 890
- 1g For C–C bond formation, see: Zhao X. Zhang Y. Wang J. Chem. Commun. 2012; 48: 10162
- 1h Qiu D. Qiu M. Ma R. Zhang Y. Wang J. Acta Chim. Sinica 2016; 74: 472
- 1i Bernardim B. Couch ED. Hardman-Baldwin AM. Burtolosa AC. B. Mattson AE. Synthesis 2016; 48: 677
- 2a Koser GF. Relenyi AG. Kalos AN. Rebrovic L. Wettach RH. J. Org. Chem. 1982; 47: 2487
- 2b Moriarty RM. Vaid RK. Koser GF. Synlett 1990; 365
- 2c Koser GF. Aldrichimica Acta 2001; 34: 89
- 3a Altermann SM. Richardson RD. Page TK. Schmidt RK. Holland E. Mohammed U. Paradine SM. French AN. Richter C. Bahar AM. Witulski B. Wirth T. Eur. J. Org. Chem. 2008; 5315
- 3b Hirt UH. Schuster MF. H. French AN. Wiest OG. Wirth T. Eur. J. Org. Chem. 2001; 1569
- 3c Hirt UH. Spingler B. Wirth T. J. Org. Chem. 1998; 63: 7674
- 3d Yusubov MS. Wirth T. Org. Lett. 2005; 7: 519
- 4a Kikui H. Moriyama K. Togo H. Synthesis 2013; 45: 791
- 4b Tanaka A. Moriyama K. Togo H. Synlett 2011; 1853
- 4c Suzuki Y. Togo H. Synlett 2010; 2355
- 4d Tanaka A. Togo H. Synlett 2009; 3360
- 4e Ishiwata Y. Togo H. Tetrahedron Lett. 2009; 50: 5354
- 4f Kawano Y. Togo H. Tetrahedron 2009; 65: 6251 ; and references cited therein
- 5a Basdevant B. Legault CY. J. Org. Chem. 2015; 80: 6897
- 5b Zhang B. Han L. Hu J. Yan J. Tetrahedron Lett. 2014; 55: 5851
- 5c Hu JT. Zhu M. Xu Y. Yan J. Synthesis 2012; 44: 1226
- 5d Mahajan US. Akamanchi KG. Synlett 2008; 937
- 5e Kumar D. Sundaree MS. Patel G. Rao VS. Varma RS. Tetrahedron Lett. 2006; 47: 8239
- 6a Chan CK. Chang M.-Y. Synlett 2016; 27: 2858 ; and references cited therein
- 6b Chan C.-K. Wang H.-S. Hsu R.-T. Chang M.-Y. Synthesis 2017; 49 ; in press; DOI: 10.1055/s-0036-1589479
- 7a Illger W. Liedhegener A. Regitz M. Liebigs Ann. Chem. 1972; 760: 1
- 7b Monteiro HJ. Synth. Commun. 1987; 17: 983
- 7c Wurz RP. Lin W. Charette AB. Tetrahedron Lett. 2003; 44: 8845
- 7d Korneev S. Richter C. Synthesis 1995; 1248
- 7e Chiara JL. Suarez JR. Adv. Synth. Catal. 2011; 353: 575
- 7f Pramanik MM. D. Rastogi N. Org. Biomol. Chem. 2015; 13: 11567
- 7g Muthyala MK. Choudhary S. Kumar A. J. Org. Chem. 2012; 77: 8787
- 7h Ferdinand G. Jeblick W. Schank K. Liebigs Ann. Chem. 1976; 1713
- 8 CCDC 1500911 (4n), 1510751 (5a), 1510750 (5d), 1519005 (5t), 1500906 (6a), 1500907 (6b) and 1515271 (9) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.
- 9a Castro CE. Gaughan EJ. Owsley DE. J. Org. Chem. 1965; 30: 587
- 9b Shi X.-X. Dai L.-X. J. Org. Chem. 1993; 58: 4596
- 9c For CuBr2, see: King LC. Ostrum GK. J. Org. Chem. 1964; 29: 3459
- 9d For CuI, see: Zhao Z. Zhang Q. Liu L. Ho Y. Li J. Li J. Zhu Q. Org. Lett. 2012; 14: 5362
- 10a Lei S. Mai Y. Yan C. Mao J. Cao H. Org. Lett. 2016; 18: 3582
- 10b Yu J. Zhang-Negrerie D. Du Y. Org. Lett. 2016; 18: 3322
- 10c Lee W.-CC. Shen Y. Gutierrez DA. Li JJ. Org. Lett. 2016; 18: 2660
- 10d Xu P. Wu Z. Zhou N. Zhu C. Org. Lett. 2016; 18: 1143
- 10e Li T. Wang Z. Xu K. Liu W. Zhang X. Mao W. Guo Y. Ge X. Pan F. Org. Lett. 2016; 18: 1064
- 10f Ouyang X.-H. Song R.-J. Liu Y. Hu M. Li J.-H. Org. Lett. 2015; 17: 6038
- 10g Miura W. Hirano K. Miura M. Org. Lett. 2015; 17: 4034
- 10h Li W. Schneider CM. Georg GI. Org. Lett. 2015; 17: 3902
- 10i Kuppusamy R. Gandeepan P. Cheng C.-H. Org. Lett. 2015; 17: 3846
- 10j Liu R.-R. Hong J.-J. Lu C.-J. Xu M. Gao J.-R. Jia Y.-X. Org. Lett. 2015; 17: 3050
- 10k Zhang J. Chen H. Wang B. Liu Z. Zhang Y. Org. Lett. 2015; 17: 2768
- 10l Mao S. Gao YR. Zhu XQ. Guo DD. Wang YQ. Org. Lett. 2015; 17: 1692
- 10m Wang H.-L. Shang M. Sun S.-Z. Zhou Z.-L. Laforteza BN. Dai H.-X. Yu J.-Q. Org. Lett. 2015; 17: 1228
- 11 Flynn CJ. Elcoate CJ. Lawrence SE. Maguire AR. J. Am. Chem. Soc. 2010; 132: 1184
- 12 H2O should come from the MeNO2 solvent. The purity of MeNO2 is 97% and it contains at least 2–3% H2O. In all experiments, all solvents (DMF, 98%; AcOH, 98%) and copper salts (>99%) were obtained from commercial sources and used without further purification.
- 13a Wang Z.-L. An X.-L. Ge L.-S. Jin J.-H. Luo X. Deng W.-P. Tetrahedron 2014; 70: 3788
- 13b Baranac-Stojanovic M. Markovic R. Stojanovic M. Tetrahedron 2011; 67: 8000
- 13c Santos MS. Coelho F. RSC Adv. 2012; 2: 3237
- 14a For NaOH/β-ketosulfones, see: Suryakiran N. Srikanth Reddy T. Suresh V. Lakshman M. Venkateswarlu Y. Tetrahedron Lett. 2006; 47: 4319
- 14b For AcOH/β-ketosulfones see: Chang M.-Y. Chan C.-K. Chen Y.-C. Heterocycles 2014; 89: 1229
- 14c For p-TsOH/β-diketones, see: Mayo MS. Yu X. Zhou X. Feng X. Yamamoto Y. Bao M. Org. Lett. 2014; 16: 764
- 14d For Cu(NO3)2/β-ketoesters, see: Steward KM. Johnson JS. Org. Lett. 2011; 13: 2426
- 15 Suryakiran N. Prabhakar P. Srikanth Reddy T. Mahesh C. Rajesh K. Venkateswarlu Y. Tetrahedron Lett. 2007; 48: 877
- 16 Reddi RN. Malekar PV. Sudalai A. Org. Biomol. Chem. 2013; 11: 6477
Selected reviews on α-functionalization of carbonyl compounds.
For C–N bond formation, see:
For others, see:
For the α-oxysulfonylation of carbonyl synthons by the Koser group, see:
For the α-oxysulfonylation of carbonyl synthons by the Wirth group, see:
For the α-oxysulfonylation of carbonyl synthons by the Togo group, see:
For the α-oxysulfonylation of carbonyl synthons by other authors, see:
For selected examples on the synthesis of α-diazo β-ketosulfones, see:
Copper halide mediated α-halogenation. For CuCl2, see:
For recent examples on Cu(OAc)2-mediated reactions, see:
For selected examples on the synthesis of vicinal tricarbonyl compounds, see:
Selected examples on carbon–carbon bond cleavage of 1,3-dicarbonyl synthons.