{"id":2652,"date":"2012-08-22T14:42:47","date_gmt":"2012-08-22T12:42:47","guid":{"rendered":"https:\/\/ospt.osi.lv\/?p=2652"},"modified":"2022-01-11T12:13:04","modified_gmt":"2022-01-11T10:13:04","slug":"indirect-c-h-azidation-of-heterocycles","status":"publish","type":"post","link":"https:\/\/ospt.osi.lv\/indirect-c-h-azidation-of-heterocycles\/","title":{"rendered":"9. Indirect C\u2013H Azidation of Heterocycles via Copper-Catalyzed Regioselective Fragmentation of Unsymmetrical \u03bb3-Iodanes"},"content":{"rendered":"<p>Lubriks, D.; Sokolovs, I.; Suna, E. <cite>J. Am. Chem. Soc.<\/cite> <strong>2012<\/strong>, <em>134<\/em>, 15436-15442.<\/p>\n<p>DOI: <a href=\"http:\/\/pubs.acs.org\/doi\/abs\/10.1021\/ja305574k\" target=\"_blank\" rel=\"noopener\">10.1021\/ja305574k <\/a><\/p>\n<p><!--more--><\/p>\n<h4>Abstract<\/h4>\n<p>A C\u2013H bond of electron-rich heterocycles is transformed into a C\u2013N bond in a reaction sequence comprising the formation of heteroaryl(phenyl)iodonium azides and their in situ regioselective fragmentation to heteroaryl azides. A Cu(I) catalyst ensures complete regiocontrol in the fragmentation step and catalyzes the subsequent 1,3-dipolar cycloaddition of the formed azido heterocycles with acetylenes. The heteroaryl azides can also be conveniently reduced to heteroarylamines by aqueous ammonium sulfide. The overall C\u2013H to C\u2013N transformation is a mild and operationally simple one-pot sequential multistep process.<\/p>\n","protected":false},"excerpt":{"rendered":"<p>Lubriks, D.; Sokolovs, I.; Suna, E. J. Am. Chem. Soc. 2012, 134, 15436-15442. DOI: 10.1021\/ja305574k<\/p>\n","protected":false},"author":1,"featured_media":2653,"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":[16,46],"tags":[],"aioseo_notices":[],"_links":{"self":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2652"}],"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=2652"}],"version-history":[{"count":1,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2652\/revisions"}],"predecessor-version":[{"id":3982,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/posts\/2652\/revisions\/3982"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/media\/2653"}],"wp:attachment":[{"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/media?parent=2652"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/categories?post=2652"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/ospt.osi.lv\/wp-json\/wp\/v2\/tags?post=2652"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}