Photocatalytic carbanion generation from C-H bonds - reductant free Barbier/Grignard-type reactions
We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radi...
Gespeichert in:
| Veröffentlicht in: | Chemical science (Cambridge) 2019, Vol.1 (48), p.1991-1996 |
|---|---|
| Hauptverfasser: | , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1996 |
|---|---|
| container_issue | 48 |
| container_start_page | 1991 |
| container_title | Chemical science (Cambridge) |
| container_volume | 1 |
| creator | Berger, Anna Lucia Donabauer, Karsten König, Burkhard |
| description | We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced
in situ
by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcohols.
We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction. |
| doi_str_mv | 10.1039/c9sc04987h |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_C9SC04987H</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2533313402</sourcerecordid><originalsourceid>FETCH-LOGICAL-c497t-2c7df63fadd2953fba91fb9a4eeb4ee19b18d8d6aaf11b2a22245663296ab4f3</originalsourceid><addsrcrecordid>eNp9kctrGzEQxkVpaUKaS-6BDb2UwDZ67UOXQrokcSHQQnIXo5e9YS25krbg_75yHByaQwfEDMxvPjTzIXRG8FeCmbjSImnMRd-t3qFjijmp24aJ94ea4iN0mtITLsEYaWj3ER0xjjnuCD9G-tcq5KAhw7TNo640RAV-DL5aWm8j5F3pYlhXQ72oVPAmVXUVrZl1Bp9Ly9rqexkabby6i-PSQzR13m5sgUDvxtMn9MHBlOzpSz5Bj7c3j8Oivv9592O4vq81F12uqe6Ma5kDY6homFMgiFMCuLWqPCIU6U1vWgBHiKJAKeVN2zIqWlDcsRP0bS-7mdXaGm19jjDJTRzXELcywCj_7fhxJZfhj-wJY5iKIvDlRSCG37NNWa7HpO00gbdhTpI2rFyw3I4W9PMb9CnM0ZftJGWU94z1FBfqck_pGFKK1h0-Q7DcuScH8TA8u7co8MUejkkfuFd35cbsVjz_H8P-AsStokM</addsrcrecordid><sourcetype>Open Access Repository</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2324833820</pqid></control><display><type>article</type><title>Photocatalytic carbanion generation from C-H bonds - reductant free Barbier/Grignard-type reactions</title><source>DOAJ Directory of Open Access Journals</source><source>PubMed Central Open Access</source><source>EZB-FREE-00999 freely available EZB journals</source><source>PubMed Central</source><creator>Berger, Anna Lucia ; Donabauer, Karsten ; König, Burkhard</creator><creatorcontrib>Berger, Anna Lucia ; Donabauer, Karsten ; König, Burkhard</creatorcontrib><description>We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced
in situ
by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcohols.
We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction.</description><identifier>ISSN: 2041-6520</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c9sc04987h</identifier><identifier>PMID: 34040714</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Alcohols ; Aldehydes ; Chemistry ; Ketones ; Photocatalysis</subject><ispartof>Chemical science (Cambridge), 2019, Vol.1 (48), p.1991-1996</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><rights>This journal is © The Royal Society of Chemistry 2019 The Royal Society of Chemistry</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c497t-2c7df63fadd2953fba91fb9a4eeb4ee19b18d8d6aaf11b2a22245663296ab4f3</citedby><cites>FETCH-LOGICAL-c497t-2c7df63fadd2953fba91fb9a4eeb4ee19b18d8d6aaf11b2a22245663296ab4f3</cites><orcidid>0000-0002-6131-4850</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8133029/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC8133029/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,4024,27923,27924,27925,53791,53793</link.rule.ids></links><search><creatorcontrib>Berger, Anna Lucia</creatorcontrib><creatorcontrib>Donabauer, Karsten</creatorcontrib><creatorcontrib>König, Burkhard</creatorcontrib><title>Photocatalytic carbanion generation from C-H bonds - reductant free Barbier/Grignard-type reactions</title><title>Chemical science (Cambridge)</title><description>We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced
in situ
by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcohols.
We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction.</description><subject>Alcohols</subject><subject>Aldehydes</subject><subject>Chemistry</subject><subject>Ketones</subject><subject>Photocatalysis</subject><issn>2041-6520</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNp9kctrGzEQxkVpaUKaS-6BDb2UwDZ67UOXQrokcSHQQnIXo5e9YS25krbg_75yHByaQwfEDMxvPjTzIXRG8FeCmbjSImnMRd-t3qFjijmp24aJ94ea4iN0mtITLsEYaWj3ER0xjjnuCD9G-tcq5KAhw7TNo640RAV-DL5aWm8j5F3pYlhXQ72oVPAmVXUVrZl1Bp9Ly9rqexkabby6i-PSQzR13m5sgUDvxtMn9MHBlOzpSz5Bj7c3j8Oivv9592O4vq81F12uqe6Ma5kDY6homFMgiFMCuLWqPCIU6U1vWgBHiKJAKeVN2zIqWlDcsRP0bS-7mdXaGm19jjDJTRzXELcywCj_7fhxJZfhj-wJY5iKIvDlRSCG37NNWa7HpO00gbdhTpI2rFyw3I4W9PMb9CnM0ZftJGWU94z1FBfqck_pGFKK1h0-Q7DcuScH8TA8u7co8MUejkkfuFd35cbsVjz_H8P-AsStokM</recordid><startdate>2019</startdate><enddate>2019</enddate><creator>Berger, Anna Lucia</creator><creator>Donabauer, Karsten</creator><creator>König, Burkhard</creator><general>Royal Society of Chemistry</general><general>The Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>5PM</scope><orcidid>https://orcid.org/0000-0002-6131-4850</orcidid></search><sort><creationdate>2019</creationdate><title>Photocatalytic carbanion generation from C-H bonds - reductant free Barbier/Grignard-type reactions</title><author>Berger, Anna Lucia ; Donabauer, Karsten ; König, Burkhard</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c497t-2c7df63fadd2953fba91fb9a4eeb4ee19b18d8d6aaf11b2a22245663296ab4f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Alcohols</topic><topic>Aldehydes</topic><topic>Chemistry</topic><topic>Ketones</topic><topic>Photocatalysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Berger, Anna Lucia</creatorcontrib><creatorcontrib>Donabauer, Karsten</creatorcontrib><creatorcontrib>König, Burkhard</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Chemical science (Cambridge)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Berger, Anna Lucia</au><au>Donabauer, Karsten</au><au>König, Burkhard</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic carbanion generation from C-H bonds - reductant free Barbier/Grignard-type reactions</atitle><jtitle>Chemical science (Cambridge)</jtitle><date>2019</date><risdate>2019</risdate><volume>1</volume><issue>48</issue><spage>1991</spage><epage>1996</epage><pages>1991-1996</pages><issn>2041-6520</issn><eissn>2041-6539</eissn><abstract>We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction. The combination of photo- and hydrogen atom transfer (HAT) catalysis enables the abstraction of a benzylic hydrogen atom, generating a radical intermediate. This radical is reduced
in situ
by the organic photocatalyst to a carbanion, which is able to react with electrophiles such as aldehydes or ketones, yielding homobenzylic secondary and tertiary alcohols.
We report a redox-neutral method for the generation of carbanions from benzylic C-H bonds in a photocatalytic Grignard-type reaction.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><pmid>34040714</pmid><doi>10.1039/c9sc04987h</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-6131-4850</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2041-6520 |
| ispartof | Chemical science (Cambridge), 2019, Vol.1 (48), p.1991-1996 |
| issn | 2041-6520 2041-6539 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_C9SC04987H |
| source | DOAJ Directory of Open Access Journals; PubMed Central Open Access; EZB-FREE-00999 freely available EZB journals; PubMed Central |
| subjects | Alcohols Aldehydes Chemistry Ketones Photocatalysis |
| title | Photocatalytic carbanion generation from C-H bonds - reductant free Barbier/Grignard-type reactions |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T20%3A21%3A33IST&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=Photocatalytic%20carbanion%20generation%20from%20C-H%20bonds%20-%20reductant%20free%20Barbier/Grignard-type%20reactions&rft.jtitle=Chemical%20science%20(Cambridge)&rft.au=Berger,%20Anna%20Lucia&rft.date=2019&rft.volume=1&rft.issue=48&rft.spage=1991&rft.epage=1996&rft.pages=1991-1996&rft.issn=2041-6520&rft.eissn=2041-6539&rft_id=info:doi/10.1039/c9sc04987h&rft_dat=%3Cproquest_cross%3E2533313402%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=2324833820&rft_id=info:pmid/34040714&rfr_iscdi=true |