Cobalt–Salen Complex-Catalyzed Oxidative Generation of Alkyl Radicals from Aldehydes for the Preparation of Hydroperoxides

Catalytic generation of alkyl radicals from aldehydes via oxidative deformylation was realized using a cobalt-salen complex with H2O2. The deformylation was thought to proceed through homolytic cleavage of peroxohemiacetal intermediates to provide even primary alkyl radicals under mild conditions. V...

Full description

Saved in:
Bibliographic Details
Published in:Journal of the American Chemical Society 2013-08, Vol.135 (32), p.11744-11747
Main Authors: Watanabe, Eiichi, Kaiho, Atsushi, Kusama, Hiroyuki, Iwasawa, Nobuharu
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-a425t-275698b300b4cc3253076ec9b118a78d43838994f3489514f057e03636416af03
cites cdi_FETCH-LOGICAL-a425t-275698b300b4cc3253076ec9b118a78d43838994f3489514f057e03636416af03
container_end_page 11747
container_issue 32
container_start_page 11744
container_title Journal of the American Chemical Society
container_volume 135
creator Watanabe, Eiichi
Kaiho, Atsushi
Kusama, Hiroyuki
Iwasawa, Nobuharu
description Catalytic generation of alkyl radicals from aldehydes via oxidative deformylation was realized using a cobalt-salen complex with H2O2. The deformylation was thought to proceed through homolytic cleavage of peroxohemiacetal intermediates to provide even primary alkyl radicals under mild conditions. Variously substituted and functionalized hydroperoxides were obtained from corresponding aldehydes in good yield.
doi_str_mv 10.1021/ja406028c
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1424322469</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1424322469</sourcerecordid><originalsourceid>FETCH-LOGICAL-a425t-275698b300b4cc3253076ec9b118a78d43838994f3489514f057e03636416af03</originalsourceid><addsrcrecordid>eNptkM1KxDAUhYMoOo4ufAHJRtBFNX9N06UUHQVB8Wdd0vYWO6ZNTTpixYXv4Bv6JEbGn42re8_lOwfuQWiHkkNKGD2aa0EkYapcQRMaMxLFlMlVNCGEsChRkm-gTe_nQQqm6DraYDwNHEsm6DWzhTbDx9v7jTbQ4cy2vYHnKNODNuMLVPjyuan00DwBnkEHLqy2w7bGx-ZhNPhaV02pjce1s224VXA_VhCkdXi4B3zloNd_prOxcrYHZ0Mo-C20VgcvbH_PKbo7PbnNzqKLy9l5dnwRacHiIWJJLFNVcEIKUZacxZwkEsq0oFTpRFWCK67SVNRcqDSmoiZxAoRLLgWVuiZ8ivaXub2zjwvwQ942vgRjdAd24XMqmOCMCZkG9GCJls5676DOe9e02o05JflX2flv2YHd_Y5dFC1Uv-RPuwHYWwK69PncLlwXvvwn6BMt54Yx</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1424322469</pqid></control><display><type>article</type><title>Cobalt–Salen Complex-Catalyzed Oxidative Generation of Alkyl Radicals from Aldehydes for the Preparation of Hydroperoxides</title><source>American Chemical Society:Jisc Collections:American Chemical Society Read &amp; Publish Agreement 2022-2024 (Reading list)</source><creator>Watanabe, Eiichi ; Kaiho, Atsushi ; Kusama, Hiroyuki ; Iwasawa, Nobuharu</creator><creatorcontrib>Watanabe, Eiichi ; Kaiho, Atsushi ; Kusama, Hiroyuki ; Iwasawa, Nobuharu</creatorcontrib><description>Catalytic generation of alkyl radicals from aldehydes via oxidative deformylation was realized using a cobalt-salen complex with H2O2. The deformylation was thought to proceed through homolytic cleavage of peroxohemiacetal intermediates to provide even primary alkyl radicals under mild conditions. Variously substituted and functionalized hydroperoxides were obtained from corresponding aldehydes in good yield.</description><identifier>ISSN: 0002-7863</identifier><identifier>EISSN: 1520-5126</identifier><identifier>DOI: 10.1021/ja406028c</identifier><identifier>PMID: 23915227</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of the American Chemical Society, 2013-08, Vol.135 (32), p.11744-11747</ispartof><rights>Copyright © 2013 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a425t-275698b300b4cc3253076ec9b118a78d43838994f3489514f057e03636416af03</citedby><cites>FETCH-LOGICAL-a425t-275698b300b4cc3253076ec9b118a78d43838994f3489514f057e03636416af03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/23915227$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Watanabe, Eiichi</creatorcontrib><creatorcontrib>Kaiho, Atsushi</creatorcontrib><creatorcontrib>Kusama, Hiroyuki</creatorcontrib><creatorcontrib>Iwasawa, Nobuharu</creatorcontrib><title>Cobalt–Salen Complex-Catalyzed Oxidative Generation of Alkyl Radicals from Aldehydes for the Preparation of Hydroperoxides</title><title>Journal of the American Chemical Society</title><addtitle>J. Am. Chem. Soc</addtitle><description>Catalytic generation of alkyl radicals from aldehydes via oxidative deformylation was realized using a cobalt-salen complex with H2O2. The deformylation was thought to proceed through homolytic cleavage of peroxohemiacetal intermediates to provide even primary alkyl radicals under mild conditions. Variously substituted and functionalized hydroperoxides were obtained from corresponding aldehydes in good yield.</description><issn>0002-7863</issn><issn>1520-5126</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNptkM1KxDAUhYMoOo4ufAHJRtBFNX9N06UUHQVB8Wdd0vYWO6ZNTTpixYXv4Bv6JEbGn42re8_lOwfuQWiHkkNKGD2aa0EkYapcQRMaMxLFlMlVNCGEsChRkm-gTe_nQQqm6DraYDwNHEsm6DWzhTbDx9v7jTbQ4cy2vYHnKNODNuMLVPjyuan00DwBnkEHLqy2w7bGx-ZhNPhaV02pjce1s224VXA_VhCkdXi4B3zloNd_prOxcrYHZ0Mo-C20VgcvbH_PKbo7PbnNzqKLy9l5dnwRacHiIWJJLFNVcEIKUZacxZwkEsq0oFTpRFWCK67SVNRcqDSmoiZxAoRLLgWVuiZ8ivaXub2zjwvwQ942vgRjdAd24XMqmOCMCZkG9GCJls5676DOe9e02o05JflX2flv2YHd_Y5dFC1Uv-RPuwHYWwK69PncLlwXvvwn6BMt54Yx</recordid><startdate>20130814</startdate><enddate>20130814</enddate><creator>Watanabe, Eiichi</creator><creator>Kaiho, Atsushi</creator><creator>Kusama, Hiroyuki</creator><creator>Iwasawa, Nobuharu</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20130814</creationdate><title>Cobalt–Salen Complex-Catalyzed Oxidative Generation of Alkyl Radicals from Aldehydes for the Preparation of Hydroperoxides</title><author>Watanabe, Eiichi ; Kaiho, Atsushi ; Kusama, Hiroyuki ; Iwasawa, Nobuharu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a425t-275698b300b4cc3253076ec9b118a78d43838994f3489514f057e03636416af03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Watanabe, Eiichi</creatorcontrib><creatorcontrib>Kaiho, Atsushi</creatorcontrib><creatorcontrib>Kusama, Hiroyuki</creatorcontrib><creatorcontrib>Iwasawa, Nobuharu</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of the American Chemical Society</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Watanabe, Eiichi</au><au>Kaiho, Atsushi</au><au>Kusama, Hiroyuki</au><au>Iwasawa, Nobuharu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cobalt–Salen Complex-Catalyzed Oxidative Generation of Alkyl Radicals from Aldehydes for the Preparation of Hydroperoxides</atitle><jtitle>Journal of the American Chemical Society</jtitle><addtitle>J. Am. Chem. Soc</addtitle><date>2013-08-14</date><risdate>2013</risdate><volume>135</volume><issue>32</issue><spage>11744</spage><epage>11747</epage><pages>11744-11747</pages><issn>0002-7863</issn><eissn>1520-5126</eissn><abstract>Catalytic generation of alkyl radicals from aldehydes via oxidative deformylation was realized using a cobalt-salen complex with H2O2. The deformylation was thought to proceed through homolytic cleavage of peroxohemiacetal intermediates to provide even primary alkyl radicals under mild conditions. Variously substituted and functionalized hydroperoxides were obtained from corresponding aldehydes in good yield.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>23915227</pmid><doi>10.1021/ja406028c</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 0002-7863
ispartof Journal of the American Chemical Society, 2013-08, Vol.135 (32), p.11744-11747
issn 0002-7863
1520-5126
language eng
recordid cdi_proquest_miscellaneous_1424322469
source American Chemical Society:Jisc Collections:American Chemical Society Read & Publish Agreement 2022-2024 (Reading list)
title Cobalt–Salen Complex-Catalyzed Oxidative Generation of Alkyl Radicals from Aldehydes for the Preparation of Hydroperoxides
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-29T11%3A37%3A03IST&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=Cobalt%E2%80%93Salen%20Complex-Catalyzed%20Oxidative%20Generation%20of%20Alkyl%20Radicals%20from%20Aldehydes%20for%20the%20Preparation%20of%20Hydroperoxides&rft.jtitle=Journal%20of%20the%20American%20Chemical%20Society&rft.au=Watanabe,%20Eiichi&rft.date=2013-08-14&rft.volume=135&rft.issue=32&rft.spage=11744&rft.epage=11747&rft.pages=11744-11747&rft.issn=0002-7863&rft.eissn=1520-5126&rft_id=info:doi/10.1021/ja406028c&rft_dat=%3Cproquest_cross%3E1424322469%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-a425t-275698b300b4cc3253076ec9b118a78d43838994f3489514f057e03636416af03%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1424322469&rft_id=info:pmid/23915227&rfr_iscdi=true