Reductive and Catalytic Monoalkylation of Primary Amines Using Nitriles as an Alkylating Reagent

A selective and catalytic mono-N-alkylation method of both aromatic and aliphatic amines using nitriles as an alkylating agent with Pd/C or Rh/C as a catalyst is described. This method is particularly attractive to provide an environmentally benign and applicable alkylation method of amines without...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2004-12, Vol.6 (26), p.4977-4980
Hauptverfasser: Sajiki, Hironao, Ikawa, Takashi, Hirota, Kosaku
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 4980
container_issue 26
container_start_page 4977
container_title Organic letters
container_volume 6
creator Sajiki, Hironao
Ikawa, Takashi
Hirota, Kosaku
description A selective and catalytic mono-N-alkylation method of both aromatic and aliphatic amines using nitriles as an alkylating agent with Pd/C or Rh/C as a catalyst is described. This method is particularly attractive to provide an environmentally benign and applicable alkylation method of amines without using toxic and corrosive alkylating agents such as alkyl halides and carbonyl compounds.
doi_str_mv 10.1021/ol047871o
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_ol047871o</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>f26393498</sourcerecordid><originalsourceid>FETCH-LOGICAL-a379t-9984bcab16b5088887d545e5da598a8db7e55233cd129c45bbe175e384ba235f3</originalsourceid><addsrcrecordid>eNptkMtOwzAQRS0EoqWw4AeQNyxYBOwkjpNlVfGSykMVXYfxI5VLalexg9S_xyhV2WCNZHvm3NHMReiSkltKUnrnWpLzklN3hMaUpVnCCUuPD--CjNCZ92tCaMxUp2hEWUEKSvMx-lxo1ctgvjUGq_AMArS7YCR-cdZB-7VrIRhnsWvwe2c20O3wdGOs9njpjV3hVxM608YvxLB4ulfEykLDSttwjk4aaL2-2N8TtHy4_5g9JfO3x-fZdJ5AxquQVFWZCwmCFoKRMh6uWM40U8CqEkoluGZxm0wqmlYyZ0JoypnOogrSjDXZBN0MfWXnvO90U2-HeWtK6l-X6oNLkb0a2G0vNlr9kXtbInA9ACB9vXZ9Z-Po_zT6AURNbvU</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Reductive and Catalytic Monoalkylation of Primary Amines Using Nitriles as an Alkylating Reagent</title><source>MEDLINE</source><source>ACS Publications</source><creator>Sajiki, Hironao ; Ikawa, Takashi ; Hirota, Kosaku</creator><creatorcontrib>Sajiki, Hironao ; Ikawa, Takashi ; Hirota, Kosaku</creatorcontrib><description>A selective and catalytic mono-N-alkylation method of both aromatic and aliphatic amines using nitriles as an alkylating agent with Pd/C or Rh/C as a catalyst is described. This method is particularly attractive to provide an environmentally benign and applicable alkylation method of amines without using toxic and corrosive alkylating agents such as alkyl halides and carbonyl compounds.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol047871o</identifier><identifier>PMID: 15606114</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Alkylation ; Amines - chemical synthesis ; Amines - chemistry ; Catalysis ; Molecular Structure ; Nitriles - chemistry ; Oxidation-Reduction</subject><ispartof>Organic letters, 2004-12, Vol.6 (26), p.4977-4980</ispartof><rights>Copyright © 2004 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a379t-9984bcab16b5088887d545e5da598a8db7e55233cd129c45bbe175e384ba235f3</citedby><cites>FETCH-LOGICAL-a379t-9984bcab16b5088887d545e5da598a8db7e55233cd129c45bbe175e384ba235f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/ol047871o$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol047871o$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2751,27055,27903,27904,56717,56767</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15606114$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Sajiki, Hironao</creatorcontrib><creatorcontrib>Ikawa, Takashi</creatorcontrib><creatorcontrib>Hirota, Kosaku</creatorcontrib><title>Reductive and Catalytic Monoalkylation of Primary Amines Using Nitriles as an Alkylating Reagent</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>A selective and catalytic mono-N-alkylation method of both aromatic and aliphatic amines using nitriles as an alkylating agent with Pd/C or Rh/C as a catalyst is described. This method is particularly attractive to provide an environmentally benign and applicable alkylation method of amines without using toxic and corrosive alkylating agents such as alkyl halides and carbonyl compounds.</description><subject>Alkylation</subject><subject>Amines - chemical synthesis</subject><subject>Amines - chemistry</subject><subject>Catalysis</subject><subject>Molecular Structure</subject><subject>Nitriles - chemistry</subject><subject>Oxidation-Reduction</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2004</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkMtOwzAQRS0EoqWw4AeQNyxYBOwkjpNlVfGSykMVXYfxI5VLalexg9S_xyhV2WCNZHvm3NHMReiSkltKUnrnWpLzklN3hMaUpVnCCUuPD--CjNCZ92tCaMxUp2hEWUEKSvMx-lxo1ctgvjUGq_AMArS7YCR-cdZB-7VrIRhnsWvwe2c20O3wdGOs9njpjV3hVxM608YvxLB4ulfEykLDSttwjk4aaL2-2N8TtHy4_5g9JfO3x-fZdJ5AxquQVFWZCwmCFoKRMh6uWM40U8CqEkoluGZxm0wqmlYyZ0JoypnOogrSjDXZBN0MfWXnvO90U2-HeWtK6l-X6oNLkb0a2G0vNlr9kXtbInA9ACB9vXZ9Z-Po_zT6AURNbvU</recordid><startdate>20041223</startdate><enddate>20041223</enddate><creator>Sajiki, Hironao</creator><creator>Ikawa, Takashi</creator><creator>Hirota, Kosaku</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20041223</creationdate><title>Reductive and Catalytic Monoalkylation of Primary Amines Using Nitriles as an Alkylating Reagent</title><author>Sajiki, Hironao ; Ikawa, Takashi ; Hirota, Kosaku</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a379t-9984bcab16b5088887d545e5da598a8db7e55233cd129c45bbe175e384ba235f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2004</creationdate><topic>Alkylation</topic><topic>Amines - chemical synthesis</topic><topic>Amines - chemistry</topic><topic>Catalysis</topic><topic>Molecular Structure</topic><topic>Nitriles - chemistry</topic><topic>Oxidation-Reduction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sajiki, Hironao</creatorcontrib><creatorcontrib>Ikawa, Takashi</creatorcontrib><creatorcontrib>Hirota, Kosaku</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sajiki, Hironao</au><au>Ikawa, Takashi</au><au>Hirota, Kosaku</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Reductive and Catalytic Monoalkylation of Primary Amines Using Nitriles as an Alkylating Reagent</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2004-12-23</date><risdate>2004</risdate><volume>6</volume><issue>26</issue><spage>4977</spage><epage>4980</epage><pages>4977-4980</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>A selective and catalytic mono-N-alkylation method of both aromatic and aliphatic amines using nitriles as an alkylating agent with Pd/C or Rh/C as a catalyst is described. This method is particularly attractive to provide an environmentally benign and applicable alkylation method of amines without using toxic and corrosive alkylating agents such as alkyl halides and carbonyl compounds.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>15606114</pmid><doi>10.1021/ol047871o</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2004-12, Vol.6 (26), p.4977-4980
issn 1523-7060
1523-7052
language eng
recordid cdi_crossref_primary_10_1021_ol047871o
source MEDLINE; ACS Publications
subjects Alkylation
Amines - chemical synthesis
Amines - chemistry
Catalysis
Molecular Structure
Nitriles - chemistry
Oxidation-Reduction
title Reductive and Catalytic Monoalkylation of Primary Amines Using Nitriles as an Alkylating Reagent
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-23T07%3A36%3A01IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Reductive%20and%20Catalytic%20Monoalkylation%20of%20Primary%20Amines%20Using%20Nitriles%20as%20an%20Alkylating%20Reagent&rft.jtitle=Organic%20letters&rft.au=Sajiki,%20Hironao&rft.date=2004-12-23&rft.volume=6&rft.issue=26&rft.spage=4977&rft.epage=4980&rft.pages=4977-4980&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol047871o&rft_dat=%3Cacs_cross%3Ef26393498%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/15606114&rfr_iscdi=true