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 2012; 44(23): 3683-3687
DOI: 10.1055/s-0032-1317500
DOI: 10.1055/s-0032-1317500
paper
General and Efficient Protocol for Formylation of Aromatic and Heterocyclic Phenols
Further Information
Publication History
Received: 03 August 2012
Accepted after revision: 02 October 2012
Publication Date:
24 October 2012 (online)
Abstract
A convenient, general procedure for formylation of diverse range of phenols with the Duff protocol has been developed. The procedure gives dialdehydes when possible.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
-
References
- 1 Jutz C. Adv. Org. Chem. 1976; 9: 225
- 2 Gattermann L, Koch JA. Ber. Dtsch. Ges. Chem. 1897; 30: 1622
- 3a Wynberg H, Meijer EW. Org. React. 1982; 28: 2
- 3b Wynberg H In Comprehensive Organic Synthesis . Vol. 2. Trost BM, Fleming I. Pergamon Press; Oxford: 1991: 769-775
- 4a Kantlehner W. Eur. J. Org. Chem. 2003; 2530
- 4b Casiraghi G, Casnati G, Puglia G, Sartori G, Terenghi G. J. Chem. Soc., Perkin Trans. 1 1980; 1862
- 4c Aldred R, Johnston R, Levin D, Neilan J. J. Chem. Soc., Perkin Trans. 1 1994; 1823
- 5a Sashidhara KV, Kumar A, Kumar M, Srivastava A, Puri A. Bioorg. Med. Chem. Lett. 2010; 20: 6504
- 5b Sashidhara KV, Kumar A, Chatterjee M, Rao KB, Singh S, Verma AK, Palit G. Bioorg. Med. Chem. Lett. 2011; 21: 1937
- 6a Chen W-H, Xing Y, Pang Y. Org. Lett. 2011; 13: 1362
- 6b Dong Y, Li J, Jiang X, Song F, Cheng Y, Zhu C. Org. Lett. 2011; 13: 2252
- 7 Koralegedara MB, Aw HW, Burns DH. J. Org. Chem. 2011; 76: 1930
- 8 O’Boyle NM, Knox AJ. S, Price TT, Williams DC, Zisterer DM, Lloyd DG, Meegan MJ. Bioorg. Med. Chem. 2011; 19: 6055
- 9a Duff JC, Bills EJ. J. Chem. Soc. 1932; 1987
- 9b Duff JC, Bills EJ. J. Chem. Soc. 1934; 1305
- 9c Duff JC, Bills EJ. J. Chem. Soc. 1941; 547
- 9d Duff JC, Bills EJ. J. Chem. Soc. 1945; 276
- 10 Smith WE. J. Org. Chem. 1972; 37: 3972
- 11a Chong JH, Sauer M, Patrick BO, MacLachlan MJ. Org. Lett. 2003; 5: 3823
- 11b Yelamaggad CV, Achalkumar AS, Rao DS. S, Prasad SK. J. Org. Chem. 2009; 74: 3168
- 11c Yelamaggad CV, Prabhu R, Rao DS. S, Prasad K. Tetrahedron Lett. 2010; 51: 4579
- 12a Anderson AA, Goetzen T, Shackelford SA, Tsank S. Synth. Commun. 2000; 30: 3227
- 12b Sashidhara KV, Rosaiah JN, Narender T. Tetrahedron Lett. 2007; 48: 1699
- 12c Ieda N, Nakagawa H, Horinouchi T, Peng T, Yang D, Tsumoto H, Suzuki T, Fukuhara K, Miyata N. Chem. Commun. 2011; 47: 6449
- 12d Yaseen M, Ali M, NajeebUllah M, Munawar MA, Khokhara I. J. Heterocycl. Chem. 2009; 46: 251
- 12e Hryniewicka A, Morzycki JW, Witkowski S. J. Organomet. Chem. 2010; 695: 1265
- 12f Nielsen M, Thomsen AH, Clo M, Kirpekar F, Gothelf KV. J. Org. Chem. 2004; 69: 2240
- 12g Sabater L, Guillot R, Aukauloo A. Tetrahedron Lett. 2005; 46: 2923
- 12h Shopsowitz KE, Edwards D, Gallant AJ, MacLachlan MJ. Tetrahedron 2009; 65: 8113
- 12i Hudecek O, Curinova P, Budka J, Lhoták P. Tetrahedron 2011; 67: 5213
- 12j Fkyerat A, Dubin G.-M, Tabacchi R. Helv. Chim. Acta 1999; 82: 1418
- 13 Richter DT, Lash TD. Tetrahedron 2001; 57: 3657
- 14 Sashidhara KV, Kumar A, Bhatia G, Khan MM, Khanna AK, Saxena JK. Eur. J. Med. Chem. 2009; 44: 1813
- 15 Fiedler H. Arch. Pharm. (Weinheim, Ger.) 1964; 297: 108
- 16 Japp FR, Meldrum AN. J. Chem. Soc. 1899; 75: 1035
- 17 Dubonosov AD. Tetrahedron 2008; 64: 3160
- 18 Dalton LK, Teitei T. Aust. J. Chem. 1969; 22: 1525
- 19 Worden LR, Burgstahler AW, Kaufman KD, Weis JA, Schaaf TK. J. Heterocycl. Chem. 1969; 6: 191