Oliver Reiser<\/a>, who led the team in Germany. The two groups were independently investigating the chemistry of \u03b1-nitroalkyl radicals\u2014the single electron species generated from nitroalkanes\u2014when they detected the formation of an alkene product under violet or blue light exposure. After several rounds of controls and repeats to confirm the observation, both teams set about optimizing their procedures and elucidating the underlying mechanism.<\/p>\n ![\"The]()
\n The structure of TBS-protected combretastatin A-4. TBS stands for tert-butyldimethylsilyl.<\/p>\n
The sequence starts by deprotonating the nitroalkane to give a nitronate anion, but the two methods differ slightly in how this intermediate then initiates the reaction, says New York University\u2019s Marvin Parasram, who led the US team. \u201cIn both our cases, though, we form an \u03b1-nitro radical that reacts with another nitronate coupling partner to form a C\u2013C bond,\u201d he says. \u201cThe resulting intermediate radical anion then goes through a single electron transfer event to eliminate NO2- and give the alkene product.\u201d Each team demonstrated the photo-stitching process on a variety of nitroalkane substrates, generating a selection of di-, tri-, and tetrasubstituted alkenes, including a protected version of the cancer drug combretastatin A-4 and an analog of temarotene, an immunosuppressive drug.<\/p>\n
![\"The]()
\n The structure of a temarotene analog.<\/p>\n
But despite the methods\u2019 similarities, they also complement each other, Reiser and Parasram say. The Reiser group\u2019s ruthenium-mediated procedure yields predominantly tetrasubstituted products, while the Parasram team\u2019s metal-free approach more effectively targets di- and trisubstituted alkenes. Operationally, the Reiser procedure is simpler, but the Parasram process uses milder conditions that tolerate a wider range of functional groups.<\/p>\n
The teams have already established a collaboration to continue working on this reaction, and a key focus of their future work will be better understanding the specific niche for each procedure. \u201cEach of them has advantages, and we want to understand better at what point you should use Marvin\u2019s versus ours. For example, do we have a different scope or different selectivity?\u201d Reiser says.<\/p>\n
Method specifics aside, the wider approach could have valuable applications in medicinal chemistry and in the generation of compound libraries, says Michael Tilby<\/a>. a synthetic chemist at the University of Bristol who was not involved in the work. “It’s a very nice way to produce these tetrasubstituted and trisubstituted species\u2014it’s not replacing a method, but it’s allowing complementary reactivity with other olefinations,\u201d he says. A key question will be unpacking how the different reaction conditions affect the final configuration of the molecule, Tilby adds. \u201cIt would be really nice to see whether future developments can introduce more stereocontrol into these reactions.”<\/p>\n","protected":false},"excerpt":{"rendered":"\u00a0 A quirky photochemical process has become the latest addition to the toolbox for making alkenes, a process…\n","protected":false},"author":2,"featured_media":590237,"comment_status":"","ping_status":"","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[7],"tags":[127892,61,60,249427,68129,82,52490],"class_list":["post-590236","post","type-post","status-publish","format-standard","has-post-thumbnail","category-science","tag-alkenes","tag-ie","tag-ireland","tag-nitro-substrates","tag-photocatalysis","tag-science","tag-synthesis"],"_links":{"self":[{"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/posts\/590236","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/comments?post=590236"}],"version-history":[{"count":0,"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/posts\/590236\/revisions"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/media\/590237"}],"wp:attachment":[{"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/media?parent=590236"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/categories?post=590236"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/www.newsbeep.com\/ie\/wp-json\/wp\/v2\/tags?post=590236"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}
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