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Aluminum Triiodide-Mediated Cleavage of o -Hydroxyphenyl Alkyl Ethers Using Inorganic Bases and Metal Oxides as Acid Scavengers

2017; Wiley; Volume: 2; Issue: 28 Linguagem: Inglês

10.1002/slct.201701685

2365-6549

Juan Tian, Cuicui Yi, Zhoujun He, Ming Yao, Dayong Sang,

Synthesis of Indole Derivatives

ChemistrySelectVolume 2, Issue 28 p. 9211-9214 Full Paper Aluminum Triiodide-Mediated Cleavage of o-Hydroxyphenyl Alkyl Ethers Using Inorganic Bases and Metal Oxides as Acid Scavengers Dr. Juan Tian, Corresponding Author Dr. Juan Tian Tianjuan2015@hotmail.com Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this authorCuicui Yi, Cuicui Yi Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this authorZhoujun He, Zhoujun He Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this authorDr. Ming Yao, Dr. Ming Yao Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this authorDr. Dayong Sang, Corresponding Author Dr. Dayong Sang Sangdy@gmail.com Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this author Dr. Juan Tian, Corresponding Author Dr. Juan Tian Tianjuan2015@hotmail.com Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this authorCuicui Yi, Cuicui Yi Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this authorZhoujun He, Zhoujun He Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this authorDr. Ming Yao, Dr. Ming Yao Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this authorDr. Dayong Sang, Corresponding Author Dr. Dayong Sang Sangdy@gmail.com Jingchu University of Technology, 33 Xiangshan Road, Jingmen, Hubei, 448000, P. R. of ChinaSearch for more papers by this author First published: 09 October 2017 https://doi.org/10.1002/slct.201701685Citations: 9Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat Graphical Abstract A proper acid scavenger is needed to prevent acid-labile functional groups from deterioration in aluminum triiodide-mediated cleavage of o-hydroxyphenyl alkyl ethers. In this work, the acid scavenging effect of inexpensive and bench stable inorganic bases and metal oxides were evaluated using eugenol as a model substrate. Among the bases and oxides screened, KOtBu, Na2CO3, CaO, CuO and ZnO were found effective. The aluminum triiodide-acid scavenger method is effective in cleaving catechol monoethers as well as general alkyl phenyl ethers. Abstract Studies have shown that a proper acid scavenger is a requisite to prevent acid-labile functional groups from deterioration during aluminum triiodide-mediated cleavage of o-hydroxyphenyl alkyl ethers. In this work, the acid scavenging effect of inexpensive and bench stable inorganic bases and metal oxides were evaluated using eugenol as a model substrate. Among the bases and oxides screened, KOtBu, Na2CO3, CaO, CuO and ZnO were found effective. The method is compatible with a variety of functional groups, and was applied successfully in cleaving catechol monoethers such as guaiacol, vanillin, isovanillin, vanillonitrile, isovanillonitrile, acetovanillone, nonivamide, ethylvanillin and o-isopropoxyphenol. The corresponding catechols were obtained in excellent yields. The oxophilicity of aluminum triiodide is not markedly suppressed by these inorganic acid scavengers, making the aluminum triiodide-acid scavenger method effective in cleaving general phenyl methyl ethers such as m-guaiacol, 4-allylanisole, veratraldehyde and methyl eugenol without the anchimeric assistance of an o-hydroxyl group. Conflict of interest The authors declare no conflict of interest. Citing Literature Supporting Information As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. Filename Description slct201701685-sup-0001-misc_information.pdf1.7 MB Supplementary Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article. Volume2, Issue28September 29, 2017Pages 9211-9214 RelatedInformation