Recent developments in transition-metal photoredox-catalysed reactions of carbonyl derivatives
Single-electron reduction of C&z.dbd;O and C&z.dbd;N bonds of aldehydes, ketones, and imines results in the formation of ketyl and α-aminoalkyl anion radicals, respectively. These reactive intermediates are characterized by an altered electronic character with respect to their parent molecul...
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Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2017-12, Vol.53 (98), p.1393-13112 |
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description | Single-electron reduction of C&z.dbd;O and C&z.dbd;N bonds of aldehydes, ketones, and imines results in the formation of ketyl and α-aminoalkyl anion radicals, respectively. These reactive intermediates are characterized by an altered electronic character with respect to their parent molecules and undergo a diverse range of synthetically useful transformations, which are not available to even-electron species. This Review summarizes the reactions of ketyl and α-aminyl radicals generated from carbonyl derivatives under transition-metal photoredox-catalysed conditions. We primarily focus on recent developments in the field, as well as give a brief overview of catalytic enantioselective transformations that provide a means to achieve precise stereocontrol over the reactivity of ion radicals.
Reactions of carbonyl derivatives induced by photocatalytic single-electron reduction of C&z.dbd;O and C&z.dbd;N bonds of aldehydes, ketones, and imines. |
doi_str_mv | 10.1039/c7cc06287g |
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Reactions of carbonyl derivatives induced by photocatalytic single-electron reduction of C&z.dbd;O and C&z.dbd;N bonds of aldehydes, ketones, and imines.</description><identifier>ISSN: 1359-7345</identifier><identifier>ISSN: 1364-548X</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/c7cc06287g</identifier><identifier>PMID: 29125152</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes ; Carbonyls ; Catalysis ; Chemical bonds ; chemical reactions ; Derivatives ; enantioselectivity ; free radicals ; Imines ; Ketones ; Radicals ; Transformations</subject><ispartof>Chemical communications (Cambridge, England), 2017-12, Vol.53 (98), p.1393-13112</ispartof><rights>Copyright Royal Society of Chemistry 2017</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c406t-c9d23cb66c9ea74d1f495ac8729870485715a8995766bc59ffa24f9f5fd162803</citedby><cites>FETCH-LOGICAL-c406t-c9d23cb66c9ea74d1f495ac8729870485715a8995766bc59ffa24f9f5fd162803</cites><orcidid>0000-0002-3055-6662 ; 0000-0003-4849-3927</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29125152$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Lee, Katarzyna N</creatorcontrib><creatorcontrib>Ngai, Ming-Yu</creatorcontrib><title>Recent developments in transition-metal photoredox-catalysed reactions of carbonyl derivatives</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Single-electron reduction of C&z.dbd;O and C&z.dbd;N bonds of aldehydes, ketones, and imines results in the formation of ketyl and α-aminoalkyl anion radicals, respectively. These reactive intermediates are characterized by an altered electronic character with respect to their parent molecules and undergo a diverse range of synthetically useful transformations, which are not available to even-electron species. This Review summarizes the reactions of ketyl and α-aminyl radicals generated from carbonyl derivatives under transition-metal photoredox-catalysed conditions. We primarily focus on recent developments in the field, as well as give a brief overview of catalytic enantioselective transformations that provide a means to achieve precise stereocontrol over the reactivity of ion radicals.
Reactions of carbonyl derivatives induced by photocatalytic single-electron reduction of C&z.dbd;O and C&z.dbd;N bonds of aldehydes, ketones, and imines.</description><subject>Aldehydes</subject><subject>Carbonyls</subject><subject>Catalysis</subject><subject>Chemical bonds</subject><subject>chemical reactions</subject><subject>Derivatives</subject><subject>enantioselectivity</subject><subject>free radicals</subject><subject>Imines</subject><subject>Ketones</subject><subject>Radicals</subject><subject>Transformations</subject><issn>1359-7345</issn><issn>1364-548X</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqF0UFLwzAYBuAgipvTi3el4EWEapImTXKUolMYCKLgyZKmiXa0TU3a4f69mZsTvJhLPpKHFz5eAI4RvEQwEVeKKQVTzNnbDhijJCUxJfxldzVTEbOE0BE48H4Ow0GU74MRFghTRPEYvD5qpds-KvVC17Zrwuyjqo16J1tf9ZVt40b3so66d9tbp0v7GSsZHpZel5HTUq2Mj6yJlHSFbZd1yHLVQvbVQvtDsGdk7fXR5p6A59ubp-wunj1M77PrWawITPtYiRInqkhTJbRkpESGCCoVZ1hwBgmnDFHJhaAsTQtFhTESEyMMNSUKi8NkAs7XuZ2zH4P2fd5UXum6lq22g88xZogTxBP0L0UiTTAjgvBAz_7QuR1cGxbJMUSQB0dJUBdrpZz13mmTd65qpFvmCOargvKMZdl3QdOATzeRQ9Hockt_GgngZA2cV9vf34aTL1colTQ</recordid><startdate>20171207</startdate><enddate>20171207</enddate><creator>Lee, Katarzyna N</creator><creator>Ngai, Ming-Yu</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><orcidid>https://orcid.org/0000-0002-3055-6662</orcidid><orcidid>https://orcid.org/0000-0003-4849-3927</orcidid></search><sort><creationdate>20171207</creationdate><title>Recent developments in transition-metal photoredox-catalysed reactions of carbonyl derivatives</title><author>Lee, Katarzyna N ; Ngai, Ming-Yu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c406t-c9d23cb66c9ea74d1f495ac8729870485715a8995766bc59ffa24f9f5fd162803</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Aldehydes</topic><topic>Carbonyls</topic><topic>Catalysis</topic><topic>Chemical bonds</topic><topic>chemical reactions</topic><topic>Derivatives</topic><topic>enantioselectivity</topic><topic>free radicals</topic><topic>Imines</topic><topic>Ketones</topic><topic>Radicals</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Lee, Katarzyna N</creatorcontrib><creatorcontrib>Ngai, Ming-Yu</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Lee, Katarzyna N</au><au>Ngai, Ming-Yu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Recent developments in transition-metal photoredox-catalysed reactions of carbonyl derivatives</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2017-12-07</date><risdate>2017</risdate><volume>53</volume><issue>98</issue><spage>1393</spage><epage>13112</epage><pages>1393-13112</pages><issn>1359-7345</issn><issn>1364-548X</issn><eissn>1364-548X</eissn><abstract>Single-electron reduction of C&z.dbd;O and C&z.dbd;N bonds of aldehydes, ketones, and imines results in the formation of ketyl and α-aminoalkyl anion radicals, respectively. These reactive intermediates are characterized by an altered electronic character with respect to their parent molecules and undergo a diverse range of synthetically useful transformations, which are not available to even-electron species. This Review summarizes the reactions of ketyl and α-aminyl radicals generated from carbonyl derivatives under transition-metal photoredox-catalysed conditions. We primarily focus on recent developments in the field, as well as give a brief overview of catalytic enantioselective transformations that provide a means to achieve precise stereocontrol over the reactivity of ion radicals.
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Aldehydes Carbonyls Catalysis Chemical bonds chemical reactions Derivatives enantioselectivity free radicals Imines Ketones Radicals Transformations |
title | Recent developments in transition-metal photoredox-catalysed reactions of carbonyl derivatives |
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