Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide–Dimethyl Sulfoxide

Dayong Sang; Juan Tian; Xiaodong Tu; Zhoujun He; Ming Yao

doi:10.1055/s-0037-1610996

Synthesis, Table of Contents

Synthesis 2019; 51(03): 704-712
DOI: 10.1055/s-0037-1610996

paper

Cleavage of Catechol Monoalkyl Ethers by Aluminum Triiodide–Dimethyl Sulfoxide

Dayong Sang

,

Juan Tian*

Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei 448000, P. R. of China Email: Tianjuan@jcut.edu.cn

,

Xiaodong Tu

,

Zhoujun He

,

Ming Yao

› Author Affiliations

Abstract

All articles of this category

Abstract

Using eugenol and vanillin as model substrates, a practical method is developed for the cleavage o-hydroxyphenyl alkyl ethers. Aluminum oxide iodide (O=AlI), generated in situ from aluminum triiodide and dimethyl sulfoxide, is the reactive ether cleaving species. The method is applicable to catechol monoalkyl ethers as well as normal phenyl alkyl ethers for the removal of methyl, ethyl, isopropyl, and benzyl groups. A variety of functional groups such as alkenyl, allyl, amide, cyano, formyl, keto, nitro, and halogen are well tolerated under the optimum conditions. Partial hydrodebromination was observed during the demethylation of 4-bromoguaiacol, and was resolved using excess DMSO as an acid scavenger. This convenient and efficient procedure would be a practical tool for the preparation of catechols.

Key words

acid scavenger - aluminum oxide iodide - demethylation - eugenol - hydrodebromination

Full Text

References

References
1 Bhatt MV. Kulkarni SU. Synthesis 1983; 249
2 Weissman SA. Zewge D. Tetrahedron 2005; 61: 7833
3 Ranu BC. Bhar S. Org. Prep. Proced. Int. 1996; 28: 371
4 Burwell RL. Jr. Chem. Rev. 1954; 54: 615
5 Zhou P. Hou A. Wang Y. Chin. J. Org. Chem. 2018; 38: 156
6 Raju GG. Raju GR. Trimurtulu G. Venkateswarlu S. Kiran B. Patent WO2009 093259, 2009
7 Lange RG. J. Org. Chem. 1962; 27: 2037
8 Lange RG. US Patent 3256336, 1966
9 Yadav Y. Owens EA. Sharma V. Aneja R. Henary M. Eur. J. Med. Chem. 2014; 75: 1
10 Shenoy NR. Choughuley AS. J. Agric. Food Chem. 1989; 37: 721
11 Jeng JH. Wang YJ. Chang WH. Wu HL. Li CH. Uang BJ. Kang JJ. Lee JJ. Hahn LJ. Lin BR. Chang MC. Cell. Mol. Life Sci. 2004; 61: 83
12 Arifin B. Tang DF. Achmadi SS. Indones. J. Chem. 2015; 15: 77
13 Fache F. Suzan N. Piva O. Tetrahedron 2005; 61: 5261
14 Kraft P. Eichenberger W. Eur. J. Org. Chem. 2003; 3735
15 Zhao H. Brandt GE. Galam L. Matts RL. Blagg BS. Bioorg. Med. Chem. Lett. 2011; 21: 2659
16 Coolen HK. Meeuwis JA. van Leeuwen PW. Nolte RJ. J. Am. Chem. Soc. 1995; 117: 11906
17 Bhatt MV. El-Morey SS. Synthesis 1982; 1048
18 Ozanne A. Pouységu L. Depernet D. Francois B. Quideau S. Org. Lett. 2003; 5: 2903
19 Pouységu L. Sylla T. Garnier T. Rojas LB. Charris J. Deffieux D. Quideau S. Tetrahedron 2010; 66: 5908
20 Strych S. Trauner D. Angew. Chem. Int. Ed. 2013; 52: 9509
21 Bernini R. Mincione E. Barontini M. Crisante F. J. Agric. Food Chem. 2008; 56: 8897
22 Andersson S. Synthesis 1985; 437
23 Tian J. Sang D. ARKIVOC 2015; (vi): 446
24 Deffieux D. Gossart P. Quideau S. Tetrahedron Lett. 2014; 55: 2455
25 Sang D. Yao M. Tian J. Chen X. Li L. Zhan H. You L. Synlett 2017; 28: 138
26 Sang D. Wang J. Zheng Y. He J. Yuan C. An Q. Tian J. Synthesis 2017; 49: 2721
27 Tian J. Yi C. Fang H. Sang D. He Z. Wang J. Gan Y. An Q. Tetrahedron Lett. 2017; 58: 3522
28 Tian J. Yi C. He Z. Yao M. Sang D. ChemistrySelect 2017; 2: 9211
29 Konwar D. Boruah RC. Sandhu JS. Tetrahedron Lett. 1990; 31: 1063
30 Sarmah P. Barua NC. Tetrahedron Lett. 1988; 29: 5815
31 Babau JR. Bhatt MV. Tetrahedron Lett. 1986; 27: 1073
32 Konwar D. Boruah RC. Sandhu JS. Synthesis 1990; 337
33 Stauber JM. Cummins CC. Inorg. Chem. 2017; 56: 3022
34 Tetsuo A. Takeshi A. Naomichi F. Shigeru O. Bull. Chem. Soc. Jpn. 1976; 49: 1441
35 Ren H. Chen Z. Cao G. Zhang F. Li H. Xu J. Miao M. Synlett 2017; 28: 1795
36 Bettanin L. Saba S. Galetto FZ. Mike GA. Rafique J. Braga AL. Tetrahedron Lett. 2017; 58: 4713
37 Rafique J. Saba S. Rosario AR. Braga AL. Chem. Eur. J. 2016; 22: 11854
38 Saba S. Rafique J. Braga AL. Catal. Sci. Technol. 2016; 6: 3087
39 Shirshova LV. Lavrent’ev IP. Russ. J. Coord. Chem. 2001; 27: 511
40 Ramanathan S. Sang D. Kumar V. Lemal DM. Synthesis of Tetrafluorocatechol . In Efficient Preparations of Fluorine Compounds . Roesky HW. Wiley; Hoboken: 2012: 252
41 Klarmann E. Gates LW. Shternov VA. J. Am. Chem. Soc. 1932; 54: 1204
42 Zuo L. Yao S. Wang W. Duan W. Tetrahedron Lett. 2008; 49: 4054
43 Fields DL. Miller JB. Reynolds DD. J. Org. Chem. 1964; 29: 2640
44 Kuwatsuka S. Casida JE. J. Agric. Food Chem. 1965; 13: 528
45 Beekman AM. Barrow RA. J. Org. Chem. 2014; 79: 1017
46 Hasse K. Willis AC. Banwell MG. Eur. J. Org. Chem. 2011; 88
47 Fazary AE. Ju Y.-H. Al-Shihri AS. Bani-Fwaz MZ. Alfaifi MY. Alshehri MA. Saleh KA. Elbehairi SE. I. Fawy KF. Abd-Rabboh HS. M. Open Chem. 2017; 15: 189
48 Sang D. Tian J. Ji G. J. Fluoresc. 2006; 16: 749

Supplementary Material

Supporting Information