Reductive Amination of Ketonic Compounds Catalyzed by CpIr(III) Complexes Bearing a Picolinamidato Ligand

Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple tran...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2019-09, Vol.84 (17), p.10962-10977
Hauptverfasser: Tanaka, Kouichi, Miki, Takashi, Murata, Kunihiko, Yamaguchi, Ayumi, Kayaki, Yoshihito, Kuwata, Shigeki, Ikariya, Takao, Watanabe, Masahito
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 10977
container_issue 17
container_start_page 10962
container_title Journal of organic chemistry
container_volume 84
creator Tanaka, Kouichi
Miki, Takashi
Murata, Kunihiko
Yamaguchi, Ayumi
Kayaki, Yoshihito
Kuwata, Shigeki
Ikariya, Takao
Watanabe, Masahito
description Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.
doi_str_mv 10.1021/acs.joc.9b01565
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2267407831</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2267407831</sourcerecordid><originalsourceid>FETCH-LOGICAL-a399t-c1ca982380716748b23012537ebbf7e545a44f9bc683afc62a4bbe961a1833ba3</originalsourceid><addsrcrecordid>eNp1kDtPwzAQgC0EoqUwsyGPRSitH3EeY4l4RFQCIZijs-NUrpK4xAmi_HoMLWzccst3n3QfQueUzChhdA7KzdZWzVJJqIjEARpTwUgQpSQ8RGNCGAs4i_gInTi3Jn6EEMdoxCmPWJgmY2SedTmo3rxrvGhMC72xLbYVftC9bY3CmW02dmhLhzPood5-6hLLLc42eTfN8_zyB6j1h3b4WkNn2hUG_GSUrb2sMSX0Fi_NCtryFB1VUDt9tt8T9Hp785LdB8vHuzxbLAPgadoHiipIE8YTEtMoDhPJOKFM8FhLWcVahALCsEqlihIOlYoYhFLqNKJAE84l8Ama7rybzr4N2vVFY5zSdQ2ttoMrGPNaEie-wQTNd6jqrHOdropNZxrotgUlxXffwvctfN9i39dfXOzlg2x0-cf_BvXA1Q7YXQ5d63_9V_cFD3eFhg</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2267407831</pqid></control><display><type>article</type><title>Reductive Amination of Ketonic Compounds Catalyzed by CpIr(III) Complexes Bearing a Picolinamidato Ligand</title><source>American Chemical Society Journals</source><creator>Tanaka, Kouichi ; Miki, Takashi ; Murata, Kunihiko ; Yamaguchi, Ayumi ; Kayaki, Yoshihito ; Kuwata, Shigeki ; Ikariya, Takao ; Watanabe, Masahito</creator><creatorcontrib>Tanaka, Kouichi ; Miki, Takashi ; Murata, Kunihiko ; Yamaguchi, Ayumi ; Kayaki, Yoshihito ; Kuwata, Shigeki ; Ikariya, Takao ; Watanabe, Masahito</creatorcontrib><description>Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.9b01565</identifier><identifier>PMID: 31362498</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2019-09, Vol.84 (17), p.10962-10977</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a399t-c1ca982380716748b23012537ebbf7e545a44f9bc683afc62a4bbe961a1833ba3</citedby><cites>FETCH-LOGICAL-a399t-c1ca982380716748b23012537ebbf7e545a44f9bc683afc62a4bbe961a1833ba3</cites><orcidid>0000-0002-3165-9882 ; 0000-0002-4685-8833</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.joc.9b01565$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.9b01565$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2765,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31362498$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Tanaka, Kouichi</creatorcontrib><creatorcontrib>Miki, Takashi</creatorcontrib><creatorcontrib>Murata, Kunihiko</creatorcontrib><creatorcontrib>Yamaguchi, Ayumi</creatorcontrib><creatorcontrib>Kayaki, Yoshihito</creatorcontrib><creatorcontrib>Kuwata, Shigeki</creatorcontrib><creatorcontrib>Ikariya, Takao</creatorcontrib><creatorcontrib>Watanabe, Masahito</creatorcontrib><title>Reductive Amination of Ketonic Compounds Catalyzed by CpIr(III) Complexes Bearing a Picolinamidato Ligand</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp1kDtPwzAQgC0EoqUwsyGPRSitH3EeY4l4RFQCIZijs-NUrpK4xAmi_HoMLWzccst3n3QfQueUzChhdA7KzdZWzVJJqIjEARpTwUgQpSQ8RGNCGAs4i_gInTi3Jn6EEMdoxCmPWJgmY2SedTmo3rxrvGhMC72xLbYVftC9bY3CmW02dmhLhzPood5-6hLLLc42eTfN8_zyB6j1h3b4WkNn2hUG_GSUrb2sMSX0Fi_NCtryFB1VUDt9tt8T9Hp785LdB8vHuzxbLAPgadoHiipIE8YTEtMoDhPJOKFM8FhLWcVahALCsEqlihIOlYoYhFLqNKJAE84l8Ama7rybzr4N2vVFY5zSdQ2ttoMrGPNaEie-wQTNd6jqrHOdropNZxrotgUlxXffwvctfN9i39dfXOzlg2x0-cf_BvXA1Q7YXQ5d63_9V_cFD3eFhg</recordid><startdate>20190906</startdate><enddate>20190906</enddate><creator>Tanaka, Kouichi</creator><creator>Miki, Takashi</creator><creator>Murata, Kunihiko</creator><creator>Yamaguchi, Ayumi</creator><creator>Kayaki, Yoshihito</creator><creator>Kuwata, Shigeki</creator><creator>Ikariya, Takao</creator><creator>Watanabe, Masahito</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-3165-9882</orcidid><orcidid>https://orcid.org/0000-0002-4685-8833</orcidid></search><sort><creationdate>20190906</creationdate><title>Reductive Amination of Ketonic Compounds Catalyzed by CpIr(III) Complexes Bearing a Picolinamidato Ligand</title><author>Tanaka, Kouichi ; Miki, Takashi ; Murata, Kunihiko ; Yamaguchi, Ayumi ; Kayaki, Yoshihito ; Kuwata, Shigeki ; Ikariya, Takao ; Watanabe, Masahito</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a399t-c1ca982380716748b23012537ebbf7e545a44f9bc683afc62a4bbe961a1833ba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tanaka, Kouichi</creatorcontrib><creatorcontrib>Miki, Takashi</creatorcontrib><creatorcontrib>Murata, Kunihiko</creatorcontrib><creatorcontrib>Yamaguchi, Ayumi</creatorcontrib><creatorcontrib>Kayaki, Yoshihito</creatorcontrib><creatorcontrib>Kuwata, Shigeki</creatorcontrib><creatorcontrib>Ikariya, Takao</creatorcontrib><creatorcontrib>Watanabe, Masahito</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tanaka, Kouichi</au><au>Miki, Takashi</au><au>Murata, Kunihiko</au><au>Yamaguchi, Ayumi</au><au>Kayaki, Yoshihito</au><au>Kuwata, Shigeki</au><au>Ikariya, Takao</au><au>Watanabe, Masahito</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reductive Amination of Ketonic Compounds Catalyzed by CpIr(III) Complexes Bearing a Picolinamidato Ligand</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2019-09-06</date><risdate>2019</risdate><volume>84</volume><issue>17</issue><spage>10962</spage><epage>10977</epage><pages>10962-10977</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>Cp*Ir complexes bearing a 2-picolinamide moiety serve as effective catalysts for the direct reductive amination of ketonic compounds to give primary amines under transfer hydrogenation conditions using ammonium formate as both the nitrogen and hydrogen source. The clean and operationally simple transformation proceeds with a substrate to catalyst molar ratio (S/C) of up to 20,000 at relatively low temperature and exhibits excellent chemoselectivity toward primary amines.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>31362498</pmid><doi>10.1021/acs.joc.9b01565</doi><tpages>16</tpages><orcidid>https://orcid.org/0000-0002-3165-9882</orcidid><orcidid>https://orcid.org/0000-0002-4685-8833</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2019-09, Vol.84 (17), p.10962-10977
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_2267407831
source American Chemical Society Journals
title Reductive Amination of Ketonic Compounds Catalyzed by CpIr(III) Complexes Bearing a Picolinamidato Ligand
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T04%3A58%3A22IST&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=Reductive%20Amination%20of%20Ketonic%20Compounds%20Catalyzed%20by%20CpIr(III)%20Complexes%20Bearing%20a%20Picolinamidato%20Ligand&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Tanaka,%20Kouichi&rft.date=2019-09-06&rft.volume=84&rft.issue=17&rft.spage=10962&rft.epage=10977&rft.pages=10962-10977&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.9b01565&rft_dat=%3Cproquest_cross%3E2267407831%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=2267407831&rft_id=info:pmid/31362498&rfr_iscdi=true