Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis

Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis

Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive or...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2017-09, Vol.19 (17), p.4696-4699
Hauptverfasser: Jackl, Moritz K, Legnani, Luca, Morandi, Bill, Bode, Jeffrey W
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4699
container_issue 17
container_start_page 4696
container_title Organic letters
container_volume 19
creator Jackl, Moritz K
Legnani, Luca
Morandi, Bill
Bode, Jeffrey W
description Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins.
doi_str_mv 10.1021/acs.orglett.7b02395
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1932142638</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1932142638</sourcerecordid><originalsourceid>FETCH-LOGICAL-a390t-3f5ce417d118ed74d0b15678cd98ba62b4ede22291beed06a28bac7f610327c03</originalsourceid><addsrcrecordid>eNp9kc1OQjEQhRujEUWfwMR0iQuwP9y_JSGiJhiI6Pqmt50rNeUW294gvoYvbAno0lWnk_OdycxB6IqSASWM3grpB9a9GQhhkFWE8SI5Qmc0YbyfkYQd_9Up6aBz798JobFTnKIOy3PKaZKfoe-xbYJuWtt6PDF2gxfbJizBa49tjZ-sWy-t0Q14LBqFZ5_iC9Zi993osMQLbbS0DR6togTPnQ1WWoN7i-lofoOfQbxBE_boFDbRcyS1whMhIxdEAIXny8g4UPYTj0UQZhsnX6CTWhgPl4e3i14ndy_jh_50dv84Hk37ghck9HmdSBjSTFGag8qGilQ0SbNcqiKvRMqqIShgjBW0AlAkFSy2ZVanlHCWScK7qLf3XTv70YIP5Up7CcbEBeM9SlpwRocs5XmU8r1UOuu9g7pcO70SbltSUu7SKGMa5SGN8pBGpK4PA9pqBeqP-T1_FNzuBTv63bauifv-a_kDs4SbgQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1932142638</pqid></control><display><type>article</type><title>Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis</title><source>ACS Publications</source><creator>Jackl, Moritz K ; Legnani, Luca ; Morandi, Bill ; Bode, Jeffrey W</creator><creatorcontrib>Jackl, Moritz K ; Legnani, Luca ; Morandi, Bill ; Bode, Jeffrey W</creatorcontrib><description>Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.7b02395</identifier><identifier>PMID: 28813158</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Organic letters, 2017-09, Vol.19 (17), p.4696-4699</ispartof><rights>Copyright © 2017 American Chemical Society</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a390t-3f5ce417d118ed74d0b15678cd98ba62b4ede22291beed06a28bac7f610327c03</citedby><cites>FETCH-LOGICAL-a390t-3f5ce417d118ed74d0b15678cd98ba62b4ede22291beed06a28bac7f610327c03</cites><orcidid>0000-0001-8394-8910 ; 0000-0002-2382-7858</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.orglett.7b02395$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.7b02395$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/28813158$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jackl, Moritz K</creatorcontrib><creatorcontrib>Legnani, Luca</creatorcontrib><creatorcontrib>Morandi, Bill</creatorcontrib><creatorcontrib>Bode, Jeffrey W</creatorcontrib><title>Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins.</description><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNp9kc1OQjEQhRujEUWfwMR0iQuwP9y_JSGiJhiI6Pqmt50rNeUW294gvoYvbAno0lWnk_OdycxB6IqSASWM3grpB9a9GQhhkFWE8SI5Qmc0YbyfkYQd_9Up6aBz798JobFTnKIOy3PKaZKfoe-xbYJuWtt6PDF2gxfbJizBa49tjZ-sWy-t0Q14LBqFZ5_iC9Zi993osMQLbbS0DR6togTPnQ1WWoN7i-lofoOfQbxBE_boFDbRcyS1whMhIxdEAIXny8g4UPYTj0UQZhsnX6CTWhgPl4e3i14ndy_jh_50dv84Hk37ghck9HmdSBjSTFGag8qGilQ0SbNcqiKvRMqqIShgjBW0AlAkFSy2ZVanlHCWScK7qLf3XTv70YIP5Up7CcbEBeM9SlpwRocs5XmU8r1UOuu9g7pcO70SbltSUu7SKGMa5SGN8pBGpK4PA9pqBeqP-T1_FNzuBTv63bauifv-a_kDs4SbgQ</recordid><startdate>20170901</startdate><enddate>20170901</enddate><creator>Jackl, Moritz K</creator><creator>Legnani, Luca</creator><creator>Morandi, Bill</creator><creator>Bode, Jeffrey W</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8394-8910</orcidid><orcidid>https://orcid.org/0000-0002-2382-7858</orcidid></search><sort><creationdate>20170901</creationdate><title>Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis</title><author>Jackl, Moritz K ; Legnani, Luca ; Morandi, Bill ; Bode, Jeffrey W</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a390t-3f5ce417d118ed74d0b15678cd98ba62b4ede22291beed06a28bac7f610327c03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jackl, Moritz K</creatorcontrib><creatorcontrib>Legnani, Luca</creatorcontrib><creatorcontrib>Morandi, Bill</creatorcontrib><creatorcontrib>Bode, Jeffrey W</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Jackl, Moritz K</au><au>Legnani, Luca</au><au>Morandi, Bill</au><au>Bode, Jeffrey W</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2017-09-01</date><risdate>2017</risdate><volume>19</volume><issue>17</issue><spage>4696</spage><epage>4699</epage><pages>4696-4699</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Photocatalytic coupling of aldehydes and silicon amine protocol (SLAP) reagents enables the simple, scalable synthesis of substituted morpholines, oxazepanes, thiomorpholines, and thiazepanes under continuous flow conditions. Key to the success of this process is the combination of an inexpensive organic photocatalyst (TPP) and a Lewis acid additive, which form an amine radical cation that is easily reduced to complete the catalytic cycle. Di- and trisubstituted SLAP reagents are formed in one step by an iron-catalyzed aminoetherification of olefins.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>28813158</pmid><doi>10.1021/acs.orglett.7b02395</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0001-8394-8910</orcidid><orcidid>https://orcid.org/0000-0002-2382-7858</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2017-09, Vol.19 (17), p.4696-4699
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_1932142638
source ACS Publications
title Continuous Flow Synthesis of Morpholines and Oxazepanes with Silicon Amine Protocol (SLAP) Reagents and Lewis Acid Facilitated Photoredox Catalysis
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-12T16%3A11%3A20IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Continuous%20Flow%20Synthesis%20of%20Morpholines%20and%20Oxazepanes%20with%20Silicon%20Amine%20Protocol%20(SLAP)%20Reagents%20and%20Lewis%20Acid%20Facilitated%20Photoredox%20Catalysis&rft.jtitle=Organic%20letters&rft.au=Jackl,%20Moritz%20K&rft.date=2017-09-01&rft.volume=19&rft.issue=17&rft.spage=4696&rft.epage=4699&rft.pages=4696-4699&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.7b02395&rft_dat=%3Cproquest_cross%3E1932142638%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1932142638&rft_id=info:pmid/28813158&rfr_iscdi=true