Swift C-C bond insertion by a 12-electron palladium(0) surrogate
The selective activation of C-C bonds holds vast promise for catalysis. So far, research has been primarily directed at rhodium and nickel under harsh reaction conditions. Herein, we report C-C insertion reactions of a 12-electron palladium(0) surrogate stabilized by a cyclic(alkyl)(amino) carbene (...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2023-10, Vol.59 (81), p.1214-1217 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Breitwieser, Kevin Dankert, Fabian Grünwald, Annette Mayer, Paula R Heinemann, Frank W Munz, Dominik |
| description | The selective activation of C-C bonds holds vast promise for catalysis. So far, research has been primarily directed at rhodium and nickel under harsh reaction conditions. Herein, we report C-C insertion reactions of a 12-electron palladium(0) surrogate stabilized by a cyclic(alkyl)(amino) carbene (CAAC) ligand. Benzonitrile (1), biphenylene (2), benzocyclobutenone (3), and naphtho[
b
]cyclopropene (4) were studied. These substrates allow elucidation of the effect of ring strain as well as hybridization encompassing sp
3
, sp
2
and sp hybridized carbon atoms. All reactions proceed quantitatively at or below room temperature. This work therefore outlines perspectives for mild C-C bond functionalization catalysis.
The selective activation of C-C bonds holds vast promise for catalysis. |
| doi_str_mv | 10.1039/d3cc03964a |
| format | Article |
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b
]cyclopropene (4) were studied. These substrates allow elucidation of the effect of ring strain as well as hybridization encompassing sp
3
, sp
2
and sp hybridized carbon atoms. All reactions proceed quantitatively at or below room temperature. This work therefore outlines perspectives for mild C-C bond functionalization catalysis.
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b
]cyclopropene (4) were studied. These substrates allow elucidation of the effect of ring strain as well as hybridization encompassing sp
3
, sp
2
and sp hybridized carbon atoms. All reactions proceed quantitatively at or below room temperature. This work therefore outlines perspectives for mild C-C bond functionalization catalysis.
The selective activation of C-C bonds holds vast promise for catalysis.</description><subject>Benzonitrile</subject><subject>Catalysis</subject><subject>Covalent bonds</subject><subject>Insertion</subject><subject>Palladium</subject><subject>Rhodium</subject><subject>Room temperature</subject><subject>Substrates</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdkM1LxDAQxYMouK5evAsBLypEkyZpkptL_YQFDyp4K_mqdOk2a9Ii-9-bdUXBYeANw4-ZxwPgmOBLgqm6ctTarCXTO2BCaMkQZ_JtdzNzhQRlfB8cpLTAuQiXE3D9_Nk2A6xQBU3oHWz75OPQhh6aNdSQFMh33g4xL1a667Rrx-UZPodpjDG868Efgr1Gd8kf_egUvN7dvlQPaP50_1jN5shSjgdUNMphZ7UslJbYMuO4dqUgnkurmJVCYWs8x6wsjCfCKJebMSmxFN4QQqfgbHt3FcPH6NNQL9tkfbbU-zCmupBlKUqCOc3o6T90EcbYZ3eZEkxwnP9k6mJL2RhSir6pV7Fd6riuCa43YdY3tKq-w5xl-GQLx2R_ub-w6Re5qW42</recordid><startdate>20231010</startdate><enddate>20231010</enddate><creator>Breitwieser, Kevin</creator><creator>Dankert, Fabian</creator><creator>Grünwald, Annette</creator><creator>Mayer, Paula R</creator><creator>Heinemann, Frank W</creator><creator>Munz, Dominik</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-6806-4794</orcidid><orcidid>https://orcid.org/0000-0002-9007-8404</orcidid><orcidid>https://orcid.org/0000-0002-7012-8750</orcidid><orcidid>https://orcid.org/0000-0003-3412-651X</orcidid></search><sort><creationdate>20231010</creationdate><title>Swift C-C bond insertion by a 12-electron palladium(0) surrogate</title><author>Breitwieser, Kevin ; Dankert, Fabian ; Grünwald, Annette ; Mayer, Paula R ; Heinemann, Frank W ; Munz, Dominik</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c350t-2f9d0dca829a80c4bd5ad671e58c94c8790cbe50462be17b9db9d4488087eb113</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Benzonitrile</topic><topic>Catalysis</topic><topic>Covalent bonds</topic><topic>Insertion</topic><topic>Palladium</topic><topic>Rhodium</topic><topic>Room temperature</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Breitwieser, Kevin</creatorcontrib><creatorcontrib>Dankert, Fabian</creatorcontrib><creatorcontrib>Grünwald, Annette</creatorcontrib><creatorcontrib>Mayer, Paula R</creatorcontrib><creatorcontrib>Heinemann, Frank W</creatorcontrib><creatorcontrib>Munz, Dominik</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Breitwieser, Kevin</au><au>Dankert, Fabian</au><au>Grünwald, Annette</au><au>Mayer, Paula R</au><au>Heinemann, Frank W</au><au>Munz, Dominik</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Swift C-C bond insertion by a 12-electron palladium(0) surrogate</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2023-10-10</date><risdate>2023</risdate><volume>59</volume><issue>81</issue><spage>1214</spage><epage>1217</epage><pages>1214-1217</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The selective activation of C-C bonds holds vast promise for catalysis. So far, research has been primarily directed at rhodium and nickel under harsh reaction conditions. Herein, we report C-C insertion reactions of a 12-electron palladium(0) surrogate stabilized by a cyclic(alkyl)(amino) carbene (CAAC) ligand. Benzonitrile (1), biphenylene (2), benzocyclobutenone (3), and naphtho[
b
]cyclopropene (4) were studied. These substrates allow elucidation of the effect of ring strain as well as hybridization encompassing sp
3
, sp
2
and sp hybridized carbon atoms. All reactions proceed quantitatively at or below room temperature. This work therefore outlines perspectives for mild C-C bond functionalization catalysis.
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| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2023-10, Vol.59 (81), p.1214-1217 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_rsc_primary_d3cc03964a |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Benzonitrile Catalysis Covalent bonds Insertion Palladium Rhodium Room temperature Substrates |
| title | Swift C-C bond insertion by a 12-electron palladium(0) surrogate |
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