{"id":13612,"date":"2020-11-04T00:00:38","date_gmt":"2020-11-03T16:00:38","guid":{"rendered":"https:\/\/www.science.nus.edu.sg\/?p=13612"},"modified":"2020-11-04T15:06:51","modified_gmt":"2020-11-04T07:06:51","slug":"manipulating-chain-walking-in-olefins-using-earth-abundant-iron-based-catalysts","status":"publish","type":"post","link":"https:\/\/www.science.nus.edu.sg\/blog\/2020\/11\/manipulating-chain-walking-in-olefins-using-earth-abundant-iron-based-catalysts\/","title":{"rendered":"Manipulating chain-walking in olefins using earth-abundant iron-based catalysts"},"content":{"rendered":"<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\"><span lang=\"EN-GB\">NUS chemists have discovered a way of controlling the position of carbon-carbon double bonds (C=C) in olefin isomerisation using sustainable iron-based catalysis for potential applications in organic synthesis.<\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\"><span lang=\"EN-GB\">The catalytic isomerisation of C=C bonds is an indispensable chemical transformation used to deliver higher-value analogues. It has important uses in the chemical industry. Although a vast number of metal-catalysed C=C bond migration protocols have been developed, enduring shortcomings remain unresolved. The capability to reposition the C=C bonds within olefins, known as alkene transposition, is an efficient approach to obtain structurally isomeric forms of the same molecule from a single substrate. However, this continues to be a formidable challenge. Separately, the conversion of regioisomeric alkene mixtures which contain many isomers of the same compound to a single product having only a single isomer, is yet to be achieved. This conversion <span>is particularly useful for streamlining chemical synthesis. <\/span><br \/>\n<\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\"><span lang=\"EN-GB\">A research team led by Prof KOH Ming Joo, from the Department of Chemistry, NUS has devised a new olefin isomerisation technique in which catalytic amounts of an appropriate earth-abundant iron-based complex, a base and a boryl compound are employed to promote efficient and controllable alkene transposition (see Figure 1). This method can be used for both terminal and internal alkene substrates. Mechanistic studies by the team revealed that these chemical transformations are likely to proceed through a catalytic iron-hydride intermediate that induces C=C bond migration.<\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\"><span lang=\"EN-GB\">Prof Koh said, \u201cThe new catalytic regime provides a way to obtain structurally different products from a single substrate. Our team also found that iron-based catalysis can also be used to transform isomeric olefin mixtures, which are commonly found in petroleum-derived feedstock to a single alkene product for use by the petrochemical industry<sup>#<\/sup>.\u201d<\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\"><span lang=\"EN-GB\">\u201cThis scientific advance not only highlights a new approach for alkene chain-walking. It also illustrates the viability of controlling where the C=C bond migrates even in substrates bearing at least two possible sites that may direct the olefin isomerisation. This has significant implications to facilitate the synthesis of unsaturated moieties embedded within biologically active compounds<sup>\u01c2<\/sup>,\u201d added Prof Koh.<\/span><\/span><\/p>\n<p><span style=\"font-size: 12pt;\"><span lang=\"EN-GB\"><span style=\"font-family: arial, helvetica, sans-serif;\">The research team plans to combine this new methodology with olefin addition reactions to develop novel functionalisation transformations.<\/span> <\/span><\/span><\/p>\n<table style=\"border-collapse: collapse; width: 100%;\">\n<tbody>\n<tr>\n<td style=\"width: 28.5454%;\">\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\" lang=\"EN-GB\">Figure 1: Schematic showing the migration of the C=C bond in alkenes can be achieved using iron catalysis with less than stoichiometric amounts of a base and boryl reagent. <\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\" lang=\"EN-GB\">[Credit: Journal of the American Chemical Society]<\/span><\/p>\n<\/td>\n<td style=\"width: 71.4546%;\"><img fetchpriority=\"high\" decoding=\"async\" width=\"698\" height=\"404\" src=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_1.jpg\" alt=\"\" class=\"alignnone size-full wp-image-13606\" srcset=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_1.jpg 698w, https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_1-300x174.jpg 300w\" sizes=\"(max-width: 698px) 100vw, 698px\" \/><\/td>\n<\/tr>\n<tr>\n<td style=\"width: 28.5454%;\">\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\" lang=\"EN-GB\">Figure 2: Schematic showing the ability of iron-based catalysis in promoting regioconvergent (produces a single compound from isomeric forms of it) and regiodivergent (produces structurally isomeric forms of the same compound) olefin isomerisation. <\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\" lang=\"EN-GB\">[Credit: Journal of the American Chemical Society]<\/span><\/p>\n<\/td>\n<td style=\"width: 71.4546%;\"><img decoding=\"async\" width=\"711\" height=\"501\" src=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_2.jpg\" alt=\"\" class=\"alignnone size-full wp-image-13607\" srcset=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_2.jpg 711w, https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_2-300x211.jpg 300w\" sizes=\"(max-width: 711px) 100vw, 711px\" \/><\/td>\n<\/tr>\n<tr>\n<td style=\"width: 28.5454%;\">\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\" lang=\"EN-GB\">Figure 3: Schematic showing alkenes embedded within biologically active compounds and their precursors. <\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif; font-size: 12pt;\" lang=\"EN-GB\">[Credit: Journal of the American Chemical Society]<\/span><\/p>\n<\/td>\n<td style=\"width: 71.4546%;\"><img decoding=\"async\" width=\"960\" height=\"442\" src=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_3.jpg\" alt=\"\" class=\"alignnone size-full wp-image-13611\" srcset=\"https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_3.jpg 960w, https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_3-300x138.jpg 300w, https:\/\/www.science.nus.edu.sg\/wp-content\/uploads\/2020\/11\/256._Koh_MJ_CHM_20201019_3-768x354.jpg 768w\" sizes=\"(max-width: 960px) 100vw, 960px\" \/><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n<p><span style=\"font-family: arial, helvetica, sans-serif;\"><b><span lang=\"EN-GB\">Reference<\/span><\/b><span lang=\"EN-GB\"><\/span><\/span><\/p>\n<p><span style=\"font-family: arial, helvetica, sans-serif;\" lang=\"EN-GB\">Yu X; Zhao H; Li P; Koh MJ*, \u201cIron-catalyzed tunable and site-selective olefin transposition\u201d JOURNAL OF THE AMERICAN CHEMICAL SOCIETY Volume: 142 Issue: 42 Pages: 18223 DOI: 10.1021\/jacs.0c08631 Published: 2020.<\/span><\/p>\n<pre><span style=\"font-family: arial, helvetica, sans-serif;\" lang=\"EN-GB\">\u00a0<\/span><span style=\"font-family: arial, helvetica, sans-serif;\" lang=\"EN-GB\">Footnotes: <\/span>\r\n<span style=\"font-family: arial, helvetica, sans-serif;\"><sup><span lang=\"EN-GB\">#<\/span><\/sup><span lang=\"EN-GB\"> Refer to Figure 2. <\/span><\/span>\r\n<span style=\"font-family: arial, helvetica, sans-serif;\"><sup><span lang=\"EN-GB\">\u01c2<\/span><\/sup><span lang=\"EN-GB\"> Refer to Figure 3.<\/span><\/span><\/pre>\n<p>&nbsp;<\/p>\n","protected":false},"excerpt":{"rendered":"<p>NUS chemists have discovered a way of controlling the position of carbon-carbon double bonds (C=C) in olefin isomerisation using sustainable&#8230;<\/p>\n","protected":false},"author":16,"featured_media":13605,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"_acf_changed":false,"footnotes":""},"categories":[43,13],"tags":[],"class_list":["post-13612","post","type-post","status-publish","format-standard","has-post-thumbnail","hentry","category-catalysis","category-research-news"],"acf":[],"yoast_head":"<!-- This site is optimized with the Yoast SEO Premium plugin v23.6 (Yoast SEO v23.6) - https:\/\/yoast.com\/wordpress\/plugins\/seo\/ -->\n<title>Manipulating chain-walking in olefins using earth-abundant iron-based catalysts - NUS Faculty of Science<\/title>\n<meta name=\"robots\" content=\"index, follow, max-snippet:-1, max-image-preview:large, max-video-preview:-1\" \/>\n<link rel=\"canonical\" href=\"https:\/\/www.science.nus.edu.sg\/blog\/2020\/11\/manipulating-chain-walking-in-olefins-using-earth-abundant-iron-based-catalysts\/\" \/>\n<meta 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