C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp3 CH Activation

All you need is an open vial! The direct α arylation of cyclic alkylamines (see scheme) requires an open vial, as the hydrogen atom involved in the C(sp3)H‐activation process is ultimately released as hydrogen gas. Reports on the formation of hydrogen gas in direct transition‐metal‐catalyzed functi...

Full description

Saved in:
Bibliographic Details
Published in:Chemistry : a European journal 2010-11, Vol.16 (44), p.13063-13067
Main Authors: Prokopcová, Hana, Bergman, Sheba D., Aelvoet, Karel, Smout, Veerle, Herrebout, Wouter, Van der Veken, Benjamin, Meerpoel, Lieven, Maes, Bert U. W.
Format: Article
Language:English
Subjects:
Catalysis
CH activation
homogeneous catalysis
hydrogen
Molecular Structure
piperidines
Piperidines - chemistry
ruthenium
Ruthenium - chemistry
Stereoisomerism
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by
cites
container_end_page 13067
container_issue 44
container_start_page 13063
container_title Chemistry : a European journal
container_volume 16
creator Prokopcová, Hana
Bergman, Sheba D.
Aelvoet, Karel
Smout, Veerle
Herrebout, Wouter
Van der Veken, Benjamin
Meerpoel, Lieven
Maes, Bert U. W.
description All you need is an open vial! The direct α arylation of cyclic alkylamines (see scheme) requires an open vial, as the hydrogen atom involved in the C(sp3)H‐activation process is ultimately released as hydrogen gas. Reports on the formation of hydrogen gas in direct transition‐metal‐catalyzed functionalizations are still rare. Open‐vial reactions proved crucial to this direct arylation procedure as, upon sealing, catalyst deactivation occurs.
doi_str_mv 10.1002/chem.201001887
format article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_799798736</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>799798736</sourcerecordid><originalsourceid>FETCH-LOGICAL-i2097-f5ad34348e6409da26ca6a37e95014bcc2c7d99d41c7aa0e59d7b1dfa553e5283</originalsourceid><addsrcrecordid>eNo9kMtOwzAQRS0EgvLYskTZsTLYcWzHyxKgBVFgwWOFLNeeUkPaFDsFyu_wIXwSv0BKoZt5aM69Gl2Edik5oISkh3YIo4OUNDPNc7mCWpSnFDMp-CpqEZVJLDhTG2gzxidCiBKMraONlKicCqFa6KHAadIOs9LUvhon1SC59hMI3vkxxKQehmr6OEyOfQBbg0tughlHP0dxD2pT4sI0dfbRnOKEJcX351c3advav_76baO1gSkj7Pz1LXR7enJTdPHFVeesaF9g33wi8YAbxzKW5SAyopxJhTXCMAmKE5r1rU2tdEq5jFppDAGunOxTNzCcM-BpzrbQ_sJ3EqqXKcRaj3y0UJZmDNU0aqmUVLlkoiH3_shpfwROT4IfmTDT_4k0gFoAb76E2fJOiZ7nred562Xeuuie9JZbo8ULrY81vC-1JjxrIZnk-v6yo3tHHXFXMKrP2Q_GuIQK</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>799798736</pqid></control><display><type>article</type><title>C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp3 CH Activation</title><source>Wiley-Blackwell Read &amp; Publish Collection</source><creator>Prokopcová, Hana ; Bergman, Sheba D. ; Aelvoet, Karel ; Smout, Veerle ; Herrebout, Wouter ; Van der Veken, Benjamin ; Meerpoel, Lieven ; Maes, Bert U. W.</creator><creatorcontrib>Prokopcová, Hana ; Bergman, Sheba D. ; Aelvoet, Karel ; Smout, Veerle ; Herrebout, Wouter ; Van der Veken, Benjamin ; Meerpoel, Lieven ; Maes, Bert U. W.</creatorcontrib><description>All you need is an open vial! The direct α arylation of cyclic alkylamines (see scheme) requires an open vial, as the hydrogen atom involved in the C(sp3)H‐activation process is ultimately released as hydrogen gas. Reports on the formation of hydrogen gas in direct transition‐metal‐catalyzed functionalizations are still rare. Open‐vial reactions proved crucial to this direct arylation procedure as, upon sealing, catalyst deactivation occurs.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201001887</identifier><identifier>PMID: 20981669</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Catalysis ; CH activation ; homogeneous catalysis ; hydrogen ; Molecular Structure ; piperidines ; Piperidines - chemistry ; ruthenium ; Ruthenium - chemistry ; Stereoisomerism</subject><ispartof>Chemistry : a European journal, 2010-11, Vol.16 (44), p.13063-13067</ispartof><rights>Copyright © 2010 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/20981669$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Prokopcová, Hana</creatorcontrib><creatorcontrib>Bergman, Sheba D.</creatorcontrib><creatorcontrib>Aelvoet, Karel</creatorcontrib><creatorcontrib>Smout, Veerle</creatorcontrib><creatorcontrib>Herrebout, Wouter</creatorcontrib><creatorcontrib>Van der Veken, Benjamin</creatorcontrib><creatorcontrib>Meerpoel, Lieven</creatorcontrib><creatorcontrib>Maes, Bert U. W.</creatorcontrib><title>C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp3 CH Activation</title><title>Chemistry : a European journal</title><addtitle>Chemistry - A European Journal</addtitle><description>All you need is an open vial! The direct α arylation of cyclic alkylamines (see scheme) requires an open vial, as the hydrogen atom involved in the C(sp3)H‐activation process is ultimately released as hydrogen gas. Reports on the formation of hydrogen gas in direct transition‐metal‐catalyzed functionalizations are still rare. Open‐vial reactions proved crucial to this direct arylation procedure as, upon sealing, catalyst deactivation occurs.</description><subject>Catalysis</subject><subject>CH activation</subject><subject>homogeneous catalysis</subject><subject>hydrogen</subject><subject>Molecular Structure</subject><subject>piperidines</subject><subject>Piperidines - chemistry</subject><subject>ruthenium</subject><subject>Ruthenium - chemistry</subject><subject>Stereoisomerism</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2010</creationdate><recordtype>article</recordtype><recordid>eNo9kMtOwzAQRS0EgvLYskTZsTLYcWzHyxKgBVFgwWOFLNeeUkPaFDsFyu_wIXwSv0BKoZt5aM69Gl2Edik5oISkh3YIo4OUNDPNc7mCWpSnFDMp-CpqEZVJLDhTG2gzxidCiBKMraONlKicCqFa6KHAadIOs9LUvhon1SC59hMI3vkxxKQehmr6OEyOfQBbg0tughlHP0dxD2pT4sI0dfbRnOKEJcX351c3advav_76baO1gSkj7Pz1LXR7enJTdPHFVeesaF9g33wi8YAbxzKW5SAyopxJhTXCMAmKE5r1rU2tdEq5jFppDAGunOxTNzCcM-BpzrbQ_sJ3EqqXKcRaj3y0UJZmDNU0aqmUVLlkoiH3_shpfwROT4IfmTDT_4k0gFoAb76E2fJOiZ7nred562Xeuuie9JZbo8ULrY81vC-1JjxrIZnk-v6yo3tHHXFXMKrP2Q_GuIQK</recordid><startdate>20101122</startdate><enddate>20101122</enddate><creator>Prokopcová, Hana</creator><creator>Bergman, Sheba D.</creator><creator>Aelvoet, Karel</creator><creator>Smout, Veerle</creator><creator>Herrebout, Wouter</creator><creator>Van der Veken, Benjamin</creator><creator>Meerpoel, Lieven</creator><creator>Maes, Bert U. W.</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20101122</creationdate><title>C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp3 CH Activation</title><author>Prokopcová, Hana ; Bergman, Sheba D. ; Aelvoet, Karel ; Smout, Veerle ; Herrebout, Wouter ; Van der Veken, Benjamin ; Meerpoel, Lieven ; Maes, Bert U. W.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-i2097-f5ad34348e6409da26ca6a37e95014bcc2c7d99d41c7aa0e59d7b1dfa553e5283</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2010</creationdate><topic>Catalysis</topic><topic>CH activation</topic><topic>homogeneous catalysis</topic><topic>hydrogen</topic><topic>Molecular Structure</topic><topic>piperidines</topic><topic>Piperidines - chemistry</topic><topic>ruthenium</topic><topic>Ruthenium - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Prokopcová, Hana</creatorcontrib><creatorcontrib>Bergman, Sheba D.</creatorcontrib><creatorcontrib>Aelvoet, Karel</creatorcontrib><creatorcontrib>Smout, Veerle</creatorcontrib><creatorcontrib>Herrebout, Wouter</creatorcontrib><creatorcontrib>Van der Veken, Benjamin</creatorcontrib><creatorcontrib>Meerpoel, Lieven</creatorcontrib><creatorcontrib>Maes, Bert U. W.</creatorcontrib><collection>Istex</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Prokopcová, Hana</au><au>Bergman, Sheba D.</au><au>Aelvoet, Karel</au><au>Smout, Veerle</au><au>Herrebout, Wouter</au><au>Van der Veken, Benjamin</au><au>Meerpoel, Lieven</au><au>Maes, Bert U. W.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp3 CH Activation</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry - A European Journal</addtitle><date>2010-11-22</date><risdate>2010</risdate><volume>16</volume><issue>44</issue><spage>13063</spage><epage>13067</epage><pages>13063-13067</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>All you need is an open vial! The direct α arylation of cyclic alkylamines (see scheme) requires an open vial, as the hydrogen atom involved in the C(sp3)H‐activation process is ultimately released as hydrogen gas. Reports on the formation of hydrogen gas in direct transition‐metal‐catalyzed functionalizations are still rare. Open‐vial reactions proved crucial to this direct arylation procedure as, upon sealing, catalyst deactivation occurs.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>20981669</pmid><doi>10.1002/chem.201001887</doi><tpages>5</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0947-6539
ispartof Chemistry : a European journal, 2010-11, Vol.16 (44), p.13063-13067
issn 0947-6539
1521-3765
language eng
recordid cdi_proquest_miscellaneous_799798736
source Wiley-Blackwell Read & Publish Collection
subjects Catalysis
CH activation
homogeneous catalysis
hydrogen
Molecular Structure
piperidines
Piperidines - chemistry
ruthenium
Ruthenium - chemistry
Stereoisomerism
title C-2 Arylation of Piperidines through Directed Transition-Metal-Catalyzed sp3 CH Activation
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T15%3A22%3A42IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=C-2%20Arylation%20of%20Piperidines%20through%20Directed%20Transition-Metal-Catalyzed%20sp3%20C%EF%A3%BFH%20Activation&rft.jtitle=Chemistry%20:%20a%20European%20journal&rft.au=Prokopcov%C3%A1,%20Hana&rft.date=2010-11-22&rft.volume=16&rft.issue=44&rft.spage=13063&rft.epage=13067&rft.pages=13063-13067&rft.issn=0947-6539&rft.eissn=1521-3765&rft_id=info:doi/10.1002/chem.201001887&rft_dat=%3Cproquest_pubme%3E799798736%3C/proquest_pubme%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-i2097-f5ad34348e6409da26ca6a37e95014bcc2c7d99d41c7aa0e59d7b1dfa553e5283%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=799798736&rft_id=info:pmid/20981669&rfr_iscdi=true