Phenols, ArOH, are ubiquitous in nature, chemical testimony to the oxidizing power of the air we breathe. But chemists have always stumbled over the laboratory oxidation of arenes, ArH -> ArOH. The phenol products are easier to oxidize than the starting arenes so overoxidation rules the day.<\/p>\n
Prof. Dionicio (“Dio”) Siegel ’97<\/strong><\/a> and his collaborators have reported a breakthrough in arene oxidation in “Metal-free oxidation of aromatic carbon\u2013hydrogen bonds through a reverse-rebound mechanism,” Nature<\/em> 2013<\/strong><\/a> (DOI 10.1038\/nature12284<\/strong><\/a>). As Dio et al.<\/em> put it:<\/p>\n “Here we demonstrate that phthaloyl peroxide functions as a selective oxidant for the transformation of arenes to phenols under mild conditions. Although the reaction proceeds through a radical mechanism, aromatic C\u2013H bonds are selectively oxidized in preference to activated Csp3\u2013H bonds. Notably, a wide array of functional groups are compatible with this reaction, and this method is therefore well suited for late-stage transformations of advanced synthetic intermediates.”<\/p>\n The research, which combines experimental work from the Siegel lab at U Texas-Austin with computational studies from the Houk lab<\/strong><\/a> at UCLA, is also covered in “Easy access to phenols,” C&E News<\/strong><\/a> (News of the Week, July 15, 2013, paywall).<\/p>\n","protected":false},"excerpt":{"rendered":" Phenols, ArOH, are ubiquitous in nature, chemical testimony to the oxidizing power of the air we breathe. But chemists have always stumbled over the laboratory oxidation of arenes, ArH -> ArOH. The phenol products are easier to oxidize than the … finish reading Siegel ’97 Invents Mild Route to Phenols<\/a><\/p>\n","protected":false},"author":55,"featured_media":0,"comment_status":"open","ping_status":"closed","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[3],"tags":[],"class_list":["post-4182","post","type-post","status-publish","format-standard","hentry","category-alumni"],"_links":{"self":[{"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/posts\/4182","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/users\/55"}],"replies":[{"embeddable":true,"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/comments?post=4182"}],"version-history":[{"count":4,"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/posts\/4182\/revisions"}],"predecessor-version":[{"id":4245,"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/posts\/4182\/revisions\/4245"}],"wp:attachment":[{"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/media?parent=4182"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/categories?post=4182"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/blogs.reed.edu\/chemistry_news\/wp-json\/wp\/v2\/tags?post=4182"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}