Alkyl halide-free heteroatom alkylation and epoxidation facilitated by a recyclable polymer-supported oxidant for the in-flow preparation of diazo compounds

Chemistry - A European Journal

Volumn 21, Issue 12, 2015, Pages 4576-4579

  Nicolle, Simon M ^a   Hayes, Christopher J ^a   Moody, Christopher J ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

Author keywords

Alkylation; Carbenes; Epoxidation; Oxidation; Recyclable supported reagents

Indexed keywords

BYPRODUCTS; CHEMICAL REACTIONS; EPOXIDATION; KETONES; ORGANIC COMPOUNDS; OXIDATION;

ALKYLATION REACTIONS; CARBENES; DIAZO COMPOUNDS; EPOXIDE FORMATIONS; ORGANIC WASTES; REACTIVE METALS; RECYCLABLE POLYMERS; SUPPORTED REAGENTS;

ALKYLATION;

AMIDE; AZO COMPOUND; EPOXIDE; HALOGEN; KETONE; OXIDIZING AGENT; PHOSPHONIC ACID DERIVATIVE; PHOSPHOROUS ACID; POLYMER;

ALKYLATION; CATALYSIS; CHEMISTRY;

ALKYLATION; AMIDES; AZO COMPOUNDS; CATALYSIS; EPOXY COMPOUNDS; HALOGENS; KETONES; OXIDANTS; PHOSPHOROUS ACIDS; POLYMERS;

EID: 84924029054     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201500118     Document Type: Article

References (31)

1. J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337-2347.
2. M. P. Doyle, M. A. McKervey, T. Ye, Modern catalytic methods for organic synthesis with diazo compounds, Wiley, New York, 1998.
3. H. M. L. Davies, J. DeMeese, Tetrahedron Lett. 2001, 42, 6803-6805.
4. M. P. Doyle, W. Hu, D. J. Timmons, Org. Lett. 2001, 3, 933-935.
5. B. J. Deadman, S. G. Collins, A. R. Maguire, Chem. Eur. J. 2015, 21, 2298-2308.
6. H. E. Bartrum, D. C. Blakemore, C. J. Moody, C. J. Hayes, Chem. Eur. J. 2011, 17, 9586-9589.
7. H. E. Bartrum, D. C. Blakemore, C. J. Moody, C. J. Hayes, Tetrahedron 2013, 69, 2276-2282.
8. L. D. Proctor, A. J. Warr, Org. Proc. Res. Dev. 2002, 6, 884-892.
9. R. A. Maurya, C. P. Park, J. H. Lee, D.-P. Kim, Angew. Chem. Int. Ed. 2011, 50, 5952 -5955;
10. Angew. Chem. 2011, 123, 6074-6077.
11. F. Mastronardi, B. Gutmann, C. O. Kappe, Org. Lett. 2013, 15, 5590-5593.
12. R. C. Wheeler, O. Benali, M. Deal, E. Farrant, S. J. F. MacDonald, B. H. Warrington, Org. Proc. Res. Dev. 2007, 11, 704-710.
13. D. N. Tran, C. Battilocchio, S.-B. Lou, J. M. Hawkins, S. V. Ley, Chem. Sci. 2015, 6, 1120-1125.
14. S. M. Nicolle, C. J. Moody, Chem. Eur. J. 2014, 20, 4420-4425.
15. M. Regitz, G. Maas, Diazo Compounds. Properties and Synthesis, Academic Press, Orlando, Florida, 1986.
16. C. Soldi, K. N. Lamb, R. A. Squitieri, M. González-López, M. J. DiMaso, J. T. Shaw, J. Am. Chem. Soc. 2014, 136, 15142-15145.
17. R. Bogoczek, E. Kociolek-Balawejder, Polym. Comm. 1986, 27, 286-288.
18. D. W. Emerson, D. T. Shea, E. M. Sorensen, Ind. Eng. Chem. Proc. DD 1978, 17, 269- 274.
19. E. Kociolek-Balawejder, Polymeri 1999, 44, 674-677.
20. D. H. R. Barton, J. C. Jaszberenyi, W. Liu, T. Shinada, Tetrahedron 1996, 52, 14673-14688.
21. E. Ciganek, J. Org. Chem. 1970, 35, 862-864.
22. For a recent review on carbene X-H insertion reactions, see: D. Gillingham, N. Fei, Chem. Soc. Rev. 2013, 42, 4918-4931.
23. B. Xu, S.-F. Zhu, X.-D. Zuo, Z.-C. Zhang, Q.-L. Zhou, Angew. Chem. Int. Ed. 2014, 53, 3913 -3916;
24. Angew. Chem. 2014, 126, 3994-3997.
25. L. Ferris, D. Haigh, C. J. Moody, J. Chem. Soc. Perkin Trans. 1 1996, 2885-2888.
26. C. J. Moody, M. C. Bagley, J. Chem. Soc. Perkin Trans. 1 1998, 601-607.
27. R. T. Buck, P. A. Clarke, D. M. Coe, M. J. Drysdale, L. Ferris, D. Haigh, C. J. Moody, N. D. Pearson, E. Swann, Chem. Eur. J. 2000, 6, 2160-2167.
28. J. R. Davies, P. D. Kane, C. J. Moody, J. Org. Chem. 2005, 70, 7305-7316.
29. R. A. Hughes, S. P. Thompson, L. Alcaraz, C. J. Moody, J. Am. Chem. Soc. 2005, 127, 15644-15651.
30. D. J. Miller, C. J. Moody, Tetrahedron 1995, 51, 10811-10843.
31. A. F. Noels, A. Demonceau, N. Petiniot, A. J. Hubert, P. Teyssié , Tetrahedron 1982, 38, 2733-2739.