Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity
Serendipity has long been a welcome yet elusive phenomenon in the advancement of chemistry. We sought to exploit serendipity as a means of rapidly identifying unanticipated chemical transformations. By using a high-throughput, automated workflow and evaluating a large number of random reactions, we...
Gespeichert in:
| Veröffentlicht in: | Science (American Association for the Advancement of Science) 2011-11, Vol.334 (6059), p.1114-1117 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1117 |
|---|---|
| container_issue | 6059 |
| container_start_page | 1114 |
| container_title | Science (American Association for the Advancement of Science) |
| container_volume | 334 |
| creator | McNally, Andrew Prier, Christopher K. MacMillan, David W. C. |
| description | Serendipity has long been a welcome yet elusive phenomenon in the advancement of chemistry. We sought to exploit serendipity as a means of rapidly identifying unanticipated chemical transformations. By using a high-throughput, automated workflow and evaluating a large number of random reactions, we have discovered a photoredox-catalyzed C-H arylation reaction for the construction of benzylic amines, an important structural motif within pharmaceutical compounds that is not readily accessed via simple substrates. The mechanism directly couples tertiary amines with cyanoaromatics by using mild and operationally trivial conditions. |
| doi_str_mv | 10.1126/science.1213920 |
| format | Article |
| fullrecord | <record><control><sourceid>jstor_pubme</sourceid><recordid>TN_cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3266580</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><jstor_id>41351796</jstor_id><sourcerecordid>41351796</sourcerecordid><originalsourceid>FETCH-LOGICAL-c444t-37bfcd187689e89f1b5ef1f0b09b2cc2ff24f82e33b03507877c0303cdd67ae83</originalsourceid><addsrcrecordid>eNpVkc9uEzEQxi1ERUPhzAnkC-ppW__Ztb0XpCgUWqkSEqVHZHm949TVxg72plIeixfhmXCabSgnj_X9Zr7RfAi9o-SMUibOs_UQLJxRRnnLyAs0o6RtqlLyl2hGCBeVIrI5Rq9zviekaC1_hY4Zo1QoxWbo52efbXyAtMXRYRPwn9_VfOVDxIvqEs_TdjCjjwF_B2Mfi9vswxKPd4BvxmRGWD42zq2FAXb_Ht9AgtD7tR-3b9CRM0OGt9N7gm6_XPxYXFbX375eLebXla3reqy47JztqZJCtaBaR7sGHHWkI23HrGXOsdopBpx3hDdEKikt4YTbvhfSgOIn6NN-7nrTraC3EMpug14nvzJpq6Px-n8l-Du9jA-aMyEaRcqA02lAir82kEe9KneBYTAB4ibrlgjaFOu6kOd70qaYcwJ3cKFE7zLRUyZ6yqR0fHi-3IF_CqEAHyfAZGsGl0ywPv_jGiZrXu-s3--5-zzGdNBryhsqW8H_AgPpoXk</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>906153504</pqid></control><display><type>article</type><title>Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity</title><source>MEDLINE</source><source>JSTOR Archive Collection A-Z Listing</source><source>American Association for the Advancement of Science</source><creator>McNally, Andrew ; Prier, Christopher K. ; MacMillan, David W. C.</creator><creatorcontrib>McNally, Andrew ; Prier, Christopher K. ; MacMillan, David W. C.</creatorcontrib><description>Serendipity has long been a welcome yet elusive phenomenon in the advancement of chemistry. We sought to exploit serendipity as a means of rapidly identifying unanticipated chemical transformations. By using a high-throughput, automated workflow and evaluating a large number of random reactions, we have discovered a photoredox-catalyzed C-H arylation reaction for the construction of benzylic amines, an important structural motif within pharmaceutical compounds that is not readily accessed via simple substrates. The mechanism directly couples tertiary amines with cyanoaromatics by using mild and operationally trivial conditions.</description><identifier>ISSN: 0036-8075</identifier><identifier>EISSN: 1095-9203</identifier><identifier>DOI: 10.1126/science.1213920</identifier><identifier>PMID: 22116882</identifier><identifier>CODEN: SCIEAS</identifier><language>eng</language><publisher>Washington, DC: American Association for the Advancement of Science</publisher><subject>Amination ; Amines ; Amines - chemical synthesis ; Amines - chemistry ; Benzene Derivatives - chemical synthesis ; Benzene Derivatives - chemistry ; Carbon - chemistry ; Catalysis ; Catalysts ; Chemical reactions ; Chemicals ; Chemistry ; Exact sciences and technology ; Functional groups ; Gas Chromatography-Mass Spectrometry ; Heterocyclic Compounds - chemistry ; High-Throughput Screening Assays ; Hydrogen - chemistry ; Kinetics and mechanisms ; Noncondensed benzenic compounds ; Organic chemistry ; Organic Chemistry Phenomena ; Oxidation-Reduction ; Pharmaceutical chemistry ; Pharmaceutical preparations ; Photochemical Processes ; Preparations and properties ; Reactivity and mechanisms ; Serendipity</subject><ispartof>Science (American Association for the Advancement of Science), 2011-11, Vol.334 (6059), p.1114-1117</ispartof><rights>Copyright © 2011 American Association for the Advancement of Science</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c444t-37bfcd187689e89f1b5ef1f0b09b2cc2ff24f82e33b03507877c0303cdd67ae83</citedby><cites>FETCH-LOGICAL-c444t-37bfcd187689e89f1b5ef1f0b09b2cc2ff24f82e33b03507877c0303cdd67ae83</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.jstor.org/stable/pdf/41351796$$EPDF$$P50$$Gjstor$$H</linktopdf><linktohtml>$$Uhttps://www.jstor.org/stable/41351796$$EHTML$$P50$$Gjstor$$H</linktohtml><link.rule.ids>230,314,780,784,803,885,2884,2885,27924,27925,58017,58250</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25274344$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22116882$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>McNally, Andrew</creatorcontrib><creatorcontrib>Prier, Christopher K.</creatorcontrib><creatorcontrib>MacMillan, David W. C.</creatorcontrib><title>Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity</title><title>Science (American Association for the Advancement of Science)</title><addtitle>Science</addtitle><description>Serendipity has long been a welcome yet elusive phenomenon in the advancement of chemistry. We sought to exploit serendipity as a means of rapidly identifying unanticipated chemical transformations. By using a high-throughput, automated workflow and evaluating a large number of random reactions, we have discovered a photoredox-catalyzed C-H arylation reaction for the construction of benzylic amines, an important structural motif within pharmaceutical compounds that is not readily accessed via simple substrates. The mechanism directly couples tertiary amines with cyanoaromatics by using mild and operationally trivial conditions.</description><subject>Amination</subject><subject>Amines</subject><subject>Amines - chemical synthesis</subject><subject>Amines - chemistry</subject><subject>Benzene Derivatives - chemical synthesis</subject><subject>Benzene Derivatives - chemistry</subject><subject>Carbon - chemistry</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Chemicals</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Functional groups</subject><subject>Gas Chromatography-Mass Spectrometry</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>High-Throughput Screening Assays</subject><subject>Hydrogen - chemistry</subject><subject>Kinetics and mechanisms</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Organic Chemistry Phenomena</subject><subject>Oxidation-Reduction</subject><subject>Pharmaceutical chemistry</subject><subject>Pharmaceutical preparations</subject><subject>Photochemical Processes</subject><subject>Preparations and properties</subject><subject>Reactivity and mechanisms</subject><subject>Serendipity</subject><issn>0036-8075</issn><issn>1095-9203</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpVkc9uEzEQxi1ERUPhzAnkC-ppW__Ztb0XpCgUWqkSEqVHZHm949TVxg72plIeixfhmXCabSgnj_X9Zr7RfAi9o-SMUibOs_UQLJxRRnnLyAs0o6RtqlLyl2hGCBeVIrI5Rq9zviekaC1_hY4Zo1QoxWbo52efbXyAtMXRYRPwn9_VfOVDxIvqEs_TdjCjjwF_B2Mfi9vswxKPd4BvxmRGWD42zq2FAXb_Ht9AgtD7tR-3b9CRM0OGt9N7gm6_XPxYXFbX375eLebXla3reqy47JztqZJCtaBaR7sGHHWkI23HrGXOsdopBpx3hDdEKikt4YTbvhfSgOIn6NN-7nrTraC3EMpug14nvzJpq6Px-n8l-Du9jA-aMyEaRcqA02lAir82kEe9KneBYTAB4ibrlgjaFOu6kOd70qaYcwJ3cKFE7zLRUyZ6yqR0fHi-3IF_CqEAHyfAZGsGl0ywPv_jGiZrXu-s3--5-zzGdNBryhsqW8H_AgPpoXk</recordid><startdate>20111125</startdate><enddate>20111125</enddate><creator>McNally, Andrew</creator><creator>Prier, Christopher K.</creator><creator>MacMillan, David W. C.</creator><general>American Association for the Advancement of Science</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>5PM</scope></search><sort><creationdate>20111125</creationdate><title>Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity</title><author>McNally, Andrew ; Prier, Christopher K. ; MacMillan, David W. C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c444t-37bfcd187689e89f1b5ef1f0b09b2cc2ff24f82e33b03507877c0303cdd67ae83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Amination</topic><topic>Amines</topic><topic>Amines - chemical synthesis</topic><topic>Amines - chemistry</topic><topic>Benzene Derivatives - chemical synthesis</topic><topic>Benzene Derivatives - chemistry</topic><topic>Carbon - chemistry</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Chemicals</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Functional groups</topic><topic>Gas Chromatography-Mass Spectrometry</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>High-Throughput Screening Assays</topic><topic>Hydrogen - chemistry</topic><topic>Kinetics and mechanisms</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Organic Chemistry Phenomena</topic><topic>Oxidation-Reduction</topic><topic>Pharmaceutical chemistry</topic><topic>Pharmaceutical preparations</topic><topic>Photochemical Processes</topic><topic>Preparations and properties</topic><topic>Reactivity and mechanisms</topic><topic>Serendipity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>McNally, Andrew</creatorcontrib><creatorcontrib>Prier, Christopher K.</creatorcontrib><creatorcontrib>MacMillan, David W. C.</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Science (American Association for the Advancement of Science)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>McNally, Andrew</au><au>Prier, Christopher K.</au><au>MacMillan, David W. C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity</atitle><jtitle>Science (American Association for the Advancement of Science)</jtitle><addtitle>Science</addtitle><date>2011-11-25</date><risdate>2011</risdate><volume>334</volume><issue>6059</issue><spage>1114</spage><epage>1117</epage><pages>1114-1117</pages><issn>0036-8075</issn><eissn>1095-9203</eissn><coden>SCIEAS</coden><abstract>Serendipity has long been a welcome yet elusive phenomenon in the advancement of chemistry. We sought to exploit serendipity as a means of rapidly identifying unanticipated chemical transformations. By using a high-throughput, automated workflow and evaluating a large number of random reactions, we have discovered a photoredox-catalyzed C-H arylation reaction for the construction of benzylic amines, an important structural motif within pharmaceutical compounds that is not readily accessed via simple substrates. The mechanism directly couples tertiary amines with cyanoaromatics by using mild and operationally trivial conditions.</abstract><cop>Washington, DC</cop><pub>American Association for the Advancement of Science</pub><pmid>22116882</pmid><doi>10.1126/science.1213920</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0036-8075 |
| ispartof | Science (American Association for the Advancement of Science), 2011-11, Vol.334 (6059), p.1114-1117 |
| issn | 0036-8075 1095-9203 |
| language | eng |
| recordid | cdi_pubmedcentral_primary_oai_pubmedcentral_nih_gov_3266580 |
| source | MEDLINE; JSTOR Archive Collection A-Z Listing; American Association for the Advancement of Science |
| subjects | Amination Amines Amines - chemical synthesis Amines - chemistry Benzene Derivatives - chemical synthesis Benzene Derivatives - chemistry Carbon - chemistry Catalysis Catalysts Chemical reactions Chemicals Chemistry Exact sciences and technology Functional groups Gas Chromatography-Mass Spectrometry Heterocyclic Compounds - chemistry High-Throughput Screening Assays Hydrogen - chemistry Kinetics and mechanisms Noncondensed benzenic compounds Organic chemistry Organic Chemistry Phenomena Oxidation-Reduction Pharmaceutical chemistry Pharmaceutical preparations Photochemical Processes Preparations and properties Reactivity and mechanisms Serendipity |
| title | Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T06%3A17%3A52IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-jstor_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Discovery%20of%20an%20%CE%B1-Amino%20C-H%20Arylation%20Reaction%20Using%20the%20Strategy%20of%20Accelerated%20Serendipity&rft.jtitle=Science%20(American%20Association%20for%20the%20Advancement%20of%20Science)&rft.au=McNally,%20Andrew&rft.date=2011-11-25&rft.volume=334&rft.issue=6059&rft.spage=1114&rft.epage=1117&rft.pages=1114-1117&rft.issn=0036-8075&rft.eissn=1095-9203&rft.coden=SCIEAS&rft_id=info:doi/10.1126/science.1213920&rft_dat=%3Cjstor_pubme%3E41351796%3C/jstor_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=906153504&rft_id=info:pmid/22116882&rft_jstor_id=41351796&rfr_iscdi=true |