{"id":2686,"date":"2017-08-11T15:33:58","date_gmt":"2017-08-11T13:33:58","guid":{"rendered":"https:\/\/ospt.osi.lv\/?p=2686"},"modified":"2022-01-11T12:14:53","modified_gmt":"2022-01-11T10:14:53","slug":"synthesis-of-benzoxazoles-using-electrochemically-generated-hypervalent-iodine","status":"publish","type":"post","link":"https:\/\/ospt.osi.lv\/synthesis-of-benzoxazoles-using-electrochemically-generated-hypervalent-iodine\/","title":{"rendered":"19. Synthesis of Benzoxazoles Using Electrochemically Generated Hypervalent Iodine"},"content":{"rendered":"<p>Koleda, O.; Broese, T.; Noetzel, J.; Roemelt, M.; Suna, E.; Francke, R. <em>J. Org. Chem.<\/em> <strong>2017<\/strong>, <em>82<\/em>, 11669\u201311681.<\/p>\n<p>DOI: <a href=\"http:\/\/pubs.acs.org\/doi\/10.1021\/acs.joc.7b01686\" target=\"_blank\" rel=\"noopener\">10.1021\/acs.joc.7b01686<\/a><\/p>\n<p><!--more--><\/p>\n<p>The indirect (\u201cex-cell\u201d) electrochemical synthesis of benzoxazoles from imines using a redox mediator based on the iodine(I)\/iodine(III) redox couple is reported. Tethering the redox-active iodophenyl subunit to a tetra-alkylammonium moiety allowed for anodic oxidation to be performed without supporting electrolyte. The mediator salt can be easily recovered and reused. Our \u201cex-cell\u201d approach toward the electrosynthesis of benzoxazoles is compatible with a range of redox-sensitive functional groups. An unprecedented concerted reductive elimination mechanism for benzoxazole formation is proposed on the basis of control experiments and DFT calculations.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Koleda, O.; Broese, T.; Noetzel, J.; Roemelt, M.; Suna, E.; Francke, R. J. Org. Chem. 2017, 82, 11669\u201311681. DOI: 10.1021\/acs.joc.7b01686<\/p>\n","protected":false},"author":1,"featured_media":2687,"comment_status":"closed","ping_status":"open","sticky":false,"template":"","format":"image","meta":{"_exactmetrics_skip_tracking":false,"_exactmetrics_sitenote_active":false,"_exactmetrics_sitenote_note":"","_exactmetrics_sitenote_category":0,"footnotes":""},"categories":[43,16],"tags":[],"aioseo_notices":[],"_links":{"self":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2686"}],"collection":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/users\/1"}],"replies":[{"embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/comments?post=2686"}],"version-history":[{"count":1,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2686\/revisions"}],"predecessor-version":[{"id":3992,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2686\/revisions\/3992"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/media\/2687"}],"wp:attachment":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/media?parent=2686"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/categories?post=2686"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/tags?post=2686"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}