Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones
Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in bo...
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| Veröffentlicht in: | Chemistry : a European journal 2021-04, Vol.27 (19), p.5919-5922 |
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| container_title | Chemistry : a European journal |
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| creator | Polishchuk, Iuliia Sklyaruk, Jan Lebedev, Yury Rueping, Magnus |
| description | Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α‐position.
Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α‐position. |
| doi_str_mv | 10.1002/chem.202005508 |
| format | Article |
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Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α‐position.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202005508</identifier><identifier>PMID: 33508154</identifier><language>eng</language><publisher>Germany: Wiley Subscription Services, Inc</publisher><subject>Additives ; Amination ; Amines ; Ammonium ; Catalysts ; Chemistry ; deuteration ; Deuterium ; Direct reduction ; Inert atmospheres ; Iridium ; iridium catalysis ; Iridium compounds ; Ketones ; Phosphorus ; primary amines ; reductive amination ; Selectivity ; Urea</subject><ispartof>Chemistry : a European journal, 2021-04, Vol.27 (19), p.5919-5922</ispartof><rights>2021 Wiley‐VCH GmbH</rights><rights>2021 Wiley-VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4108-c0c4a6b62a107b17d40b97a720ce6cc97970d4a463441a9973347d34209e6a5e3</citedby><cites>FETCH-LOGICAL-c4108-c0c4a6b62a107b17d40b97a720ce6cc97970d4a463441a9973347d34209e6a5e3</cites><orcidid>0000-0003-2985-6876 ; 0000-0003-4580-5227 ; 0000-0002-8622-0455</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.202005508$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202005508$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33508154$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Polishchuk, Iuliia</creatorcontrib><creatorcontrib>Sklyaruk, Jan</creatorcontrib><creatorcontrib>Lebedev, Yury</creatorcontrib><creatorcontrib>Rueping, Magnus</creatorcontrib><title>Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α‐position.
Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α‐position.</description><subject>Additives</subject><subject>Amination</subject><subject>Amines</subject><subject>Ammonium</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>deuteration</subject><subject>Deuterium</subject><subject>Direct reduction</subject><subject>Inert atmospheres</subject><subject>Iridium</subject><subject>iridium catalysis</subject><subject>Iridium compounds</subject><subject>Ketones</subject><subject>Phosphorus</subject><subject>primary amines</subject><subject>reductive amination</subject><subject>Selectivity</subject><subject>Urea</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqF0LlLBDEUx_Egiq5HaykBG5tZX45JJuWynqgIHnXIZN5iZA5NZpT97x1ZD7CxSvPJl8ePkH0GUwbAj_0TNlMOHCDPoVgjE5Zzlgmt8nUyASN1pnJhtsh2Ss8AYJQQm2RLiBGzXE7I2SxEet-7skZ6GUMVhobOXe_qZeoTXXSRnoSIvqd3WA2-D29IZ01oXR-6lnYLeoV912LaJRsLVyfc-3p3yOPZ6cP8Iru-Pb-cz64zLxkUmQcvnSoVdwx0yXQloTTaaQ4elfdGGw2VdFIJKZkzRgshdSUkB4PK5Sh2yNGq-xK71wFTb5uQPNa1a7EbkuWyEAWTjBcjPfxDn7shtuN1ludgOAel9aimK-Vjl1LEhX2JoXFxaRnYz4Xt58L2Z-Hxw8FXdigbrH7496QjMCvwHmpc_pOz84vTm9_4B4VLhPA</recordid><startdate>20210401</startdate><enddate>20210401</enddate><creator>Polishchuk, Iuliia</creator><creator>Sklyaruk, Jan</creator><creator>Lebedev, Yury</creator><creator>Rueping, Magnus</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-2985-6876</orcidid><orcidid>https://orcid.org/0000-0003-4580-5227</orcidid><orcidid>https://orcid.org/0000-0002-8622-0455</orcidid></search><sort><creationdate>20210401</creationdate><title>Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones</title><author>Polishchuk, Iuliia ; Sklyaruk, Jan ; Lebedev, Yury ; Rueping, Magnus</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4108-c0c4a6b62a107b17d40b97a720ce6cc97970d4a463441a9973347d34209e6a5e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Additives</topic><topic>Amination</topic><topic>Amines</topic><topic>Ammonium</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>deuteration</topic><topic>Deuterium</topic><topic>Direct reduction</topic><topic>Inert atmospheres</topic><topic>Iridium</topic><topic>iridium catalysis</topic><topic>Iridium compounds</topic><topic>Ketones</topic><topic>Phosphorus</topic><topic>primary amines</topic><topic>reductive amination</topic><topic>Selectivity</topic><topic>Urea</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Polishchuk, Iuliia</creatorcontrib><creatorcontrib>Sklyaruk, Jan</creatorcontrib><creatorcontrib>Lebedev, Yury</creatorcontrib><creatorcontrib>Rueping, Magnus</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Polishchuk, Iuliia</au><au>Sklyaruk, Jan</au><au>Lebedev, Yury</au><au>Rueping, Magnus</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2021-04-01</date><risdate>2021</risdate><volume>27</volume><issue>19</issue><spage>5919</spage><epage>5922</epage><pages>5919-5922</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. One of the complexes was found to be active in both the Leuckart–Wallach (NH4CO2H) type reaction as well as in the hydrogenative (H2/NH4AcO) reductive amination. The protocol with ammonium formate does not require an inert atmosphere, dry solvents, as well as additives and in contrast to previous reports takes place in hexafluoroisopropanol (HFIP) instead of methanol. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α‐position.
Half‐sandwich iridium complexes bearing bidentate urea‐phosphorus ligands were found to catalyze the direct reductive amination of aromatic and aliphatic ketones under mild conditions at 0.5 mol % loading with high selectivity towards primary amines. Applying NH4CO2D or D2 resulted in a high degree of deuterium incorporation into the primary amine α‐position.</abstract><cop>Germany</cop><pub>Wiley Subscription Services, Inc</pub><pmid>33508154</pmid><doi>10.1002/chem.202005508</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-2985-6876</orcidid><orcidid>https://orcid.org/0000-0003-4580-5227</orcidid><orcidid>https://orcid.org/0000-0002-8622-0455</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Additives Amination Amines Ammonium Catalysts Chemistry deuteration Deuterium Direct reduction Inert atmospheres Iridium iridium catalysis Iridium compounds Ketones Phosphorus primary amines reductive amination Selectivity Urea |
| title | Air Stable Iridium Catalysts for Direct Reductive Amination of Ketones |
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