A mesoionic carbene stabilized nickel() hydroxide complex: a facile precursor for C-H activation chemistry
We report the synthesis of a new nickel( ii ) hydroxide complex 2 supported by a rigid, tridentate triazolylidene-carbazolid ligand. The complex can be accessed in high yields following a simple and stepwise extraction protocol using dichloromethane and aqueous ammonium chloride followed by aqeous s...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2024-02, Vol.53 (6), p.2749-2761 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Pavun, Anna Niess, Raffael Scheibel, Lucas A Seidl, Michael Hohloch, Stephan |
| description | We report the synthesis of a new nickel(
ii
) hydroxide complex
2
supported by a rigid, tridentate triazolylidene-carbazolid ligand. The complex can be accessed in high yields following a simple and stepwise extraction protocol using dichloromethane and aqueous ammonium chloride followed by aqeous sodium hydroxide solution. We found that complex
2
is highly basic, undergoing various deprotonation/desilylation reactions with E-H and C-H acidic and silylated compounds. In this context we synthesized a variety of novel, functionalized nickel(
ii
) complexes with trimethylsilylolate (
3
), trityl sulfide (
4
), tosyl amide (
5
), azido (
6
), pyridine (
7
), acetylide (
8
,
9
), fluoroarene (
10
&
11
) and enolate (
12
) ligands. We furthermore found that
2
reacts with malonic acid dimethyl ester in a knoevennagel-type condensation reaction, giving access to a new enolate ligand in complex
13
, consisting of two malonic acid units. Furthermore, complex
2
reacts with acetonitrile to form the cyanido complex
14
. The formation of complexes
13
and
14
is particularly interesting, as they underline the potential of complex
2
in both C-C bond formation and cleavage reactions.
We report the synthesis of a nickel(
ii
) hydroxide complex
2
supported by a rigid, tridentate triazolylidene-carbazolid ligand, acting as a versatile precursor to perform E-H (E = O, S, N) and C-H activation reactions. |
| doi_str_mv | 10.1039/d3dt03746k |
| format | Article |
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ii
) hydroxide complex
2
supported by a rigid, tridentate triazolylidene-carbazolid ligand. The complex can be accessed in high yields following a simple and stepwise extraction protocol using dichloromethane and aqueous ammonium chloride followed by aqeous sodium hydroxide solution. We found that complex
2
is highly basic, undergoing various deprotonation/desilylation reactions with E-H and C-H acidic and silylated compounds. In this context we synthesized a variety of novel, functionalized nickel(
ii
) complexes with trimethylsilylolate (
3
), trityl sulfide (
4
), tosyl amide (
5
), azido (
6
), pyridine (
7
), acetylide (
8
,
9
), fluoroarene (
10
&
11
) and enolate (
12
) ligands. We furthermore found that
2
reacts with malonic acid dimethyl ester in a knoevennagel-type condensation reaction, giving access to a new enolate ligand in complex
13
, consisting of two malonic acid units. Furthermore, complex
2
reacts with acetonitrile to form the cyanido complex
14
. The formation of complexes
13
and
14
is particularly interesting, as they underline the potential of complex
2
in both C-C bond formation and cleavage reactions.
We report the synthesis of a nickel(
ii
) hydroxide complex
2
supported by a rigid, tridentate triazolylidene-carbazolid ligand, acting as a versatile precursor to perform E-H (E = O, S, N) and C-H activation reactions.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d3dt03746k</identifier><identifier>PMID: 38226674</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Acetonitrile ; Ammonium chloride ; Chemical synthesis ; Covalent bonds ; Dichloromethane ; Ligands ; Nickel compounds ; Sodium hydroxide</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2024-02, Vol.53 (6), p.2749-2761</ispartof><rights>Copyright Royal Society of Chemistry 2024</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c332t-829ef55de21068b9d98e4094bfafb2e960d647028400bf324c092c9716f7f2673</cites><orcidid>0000-0002-1876-2746 ; 0000-0002-5353-0801</orcidid></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/38226674$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Pavun, Anna</creatorcontrib><creatorcontrib>Niess, Raffael</creatorcontrib><creatorcontrib>Scheibel, Lucas A</creatorcontrib><creatorcontrib>Seidl, Michael</creatorcontrib><creatorcontrib>Hohloch, Stephan</creatorcontrib><title>A mesoionic carbene stabilized nickel() hydroxide complex: a facile precursor for C-H activation chemistry</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>We report the synthesis of a new nickel(
ii
) hydroxide complex
2
supported by a rigid, tridentate triazolylidene-carbazolid ligand. The complex can be accessed in high yields following a simple and stepwise extraction protocol using dichloromethane and aqueous ammonium chloride followed by aqeous sodium hydroxide solution. We found that complex
2
is highly basic, undergoing various deprotonation/desilylation reactions with E-H and C-H acidic and silylated compounds. In this context we synthesized a variety of novel, functionalized nickel(
ii
) complexes with trimethylsilylolate (
3
), trityl sulfide (
4
), tosyl amide (
5
), azido (
6
), pyridine (
7
), acetylide (
8
,
9
), fluoroarene (
10
&
11
) and enolate (
12
) ligands. We furthermore found that
2
reacts with malonic acid dimethyl ester in a knoevennagel-type condensation reaction, giving access to a new enolate ligand in complex
13
, consisting of two malonic acid units. Furthermore, complex
2
reacts with acetonitrile to form the cyanido complex
14
. The formation of complexes
13
and
14
is particularly interesting, as they underline the potential of complex
2
in both C-C bond formation and cleavage reactions.
We report the synthesis of a nickel(
ii
) hydroxide complex
2
supported by a rigid, tridentate triazolylidene-carbazolid ligand, acting as a versatile precursor to perform E-H (E = O, S, N) and C-H activation reactions.</description><subject>Acetonitrile</subject><subject>Ammonium chloride</subject><subject>Chemical synthesis</subject><subject>Covalent bonds</subject><subject>Dichloromethane</subject><subject>Ligands</subject><subject>Nickel compounds</subject><subject>Sodium hydroxide</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkU1LxDAQhoMofl-8KwEvKlTTJE0bb8v6iYIXPZc0mWDWdrMmrbj-eqOrK3gYZph5eGeYF6G9nJzmhMkzw0xPWMnFywrazHlZZpIyvrqsqdhAWzFOCKGUFHQdbbAqNUXJN9FkhDuI3vmp01ir0MAUcOxV41r3AQan9gu0R8f4eW6Cf3cGsPbdrIX3c6ywVdq1gGcB9BCiD9imGGc3WOnevak-yWL9DJ2LfZjvoDWr2gi7P3kbPV1dPo5vsvuH69vx6D7TjNE-q6gEWxQGaE5E1UgjK-BE8sYq21CQghjBS0IrTkhjGeWaSKplmQtbWipKto2OFrqz4F8HiH2d9mtoWzUFP8SayrwohEyfSOjhP3TihzBN1yWKUlZwyXmiThaUDj7GALaeBdepMK9zUn85UF-wi8dvB-4SfPAjOTQdmCX6-_IE7C-AEPVy-mch-wSKHonV</recordid><startdate>20240206</startdate><enddate>20240206</enddate><creator>Pavun, Anna</creator><creator>Niess, Raffael</creator><creator>Scheibel, Lucas A</creator><creator>Seidl, Michael</creator><creator>Hohloch, Stephan</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><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/0000-0002-1876-2746</orcidid><orcidid>https://orcid.org/0000-0002-5353-0801</orcidid></search><sort><creationdate>20240206</creationdate><title>A mesoionic carbene stabilized nickel() hydroxide complex: a facile precursor for C-H activation chemistry</title><author>Pavun, Anna ; Niess, Raffael ; Scheibel, Lucas A ; Seidl, Michael ; Hohloch, Stephan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c332t-829ef55de21068b9d98e4094bfafb2e960d647028400bf324c092c9716f7f2673</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Acetonitrile</topic><topic>Ammonium chloride</topic><topic>Chemical synthesis</topic><topic>Covalent bonds</topic><topic>Dichloromethane</topic><topic>Ligands</topic><topic>Nickel compounds</topic><topic>Sodium hydroxide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Pavun, Anna</creatorcontrib><creatorcontrib>Niess, Raffael</creatorcontrib><creatorcontrib>Scheibel, Lucas A</creatorcontrib><creatorcontrib>Seidl, Michael</creatorcontrib><creatorcontrib>Hohloch, Stephan</creatorcontrib><collection>PubMed</collection><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>Dalton transactions : an international journal of inorganic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Pavun, Anna</au><au>Niess, Raffael</au><au>Scheibel, Lucas A</au><au>Seidl, Michael</au><au>Hohloch, Stephan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A mesoionic carbene stabilized nickel() hydroxide complex: a facile precursor for C-H activation chemistry</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2024-02-06</date><risdate>2024</risdate><volume>53</volume><issue>6</issue><spage>2749</spage><epage>2761</epage><pages>2749-2761</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>We report the synthesis of a new nickel(
ii
) hydroxide complex
2
supported by a rigid, tridentate triazolylidene-carbazolid ligand. The complex can be accessed in high yields following a simple and stepwise extraction protocol using dichloromethane and aqueous ammonium chloride followed by aqeous sodium hydroxide solution. We found that complex
2
is highly basic, undergoing various deprotonation/desilylation reactions with E-H and C-H acidic and silylated compounds. In this context we synthesized a variety of novel, functionalized nickel(
ii
) complexes with trimethylsilylolate (
3
), trityl sulfide (
4
), tosyl amide (
5
), azido (
6
), pyridine (
7
), acetylide (
8
,
9
), fluoroarene (
10
&
11
) and enolate (
12
) ligands. We furthermore found that
2
reacts with malonic acid dimethyl ester in a knoevennagel-type condensation reaction, giving access to a new enolate ligand in complex
13
, consisting of two malonic acid units. Furthermore, complex
2
reacts with acetonitrile to form the cyanido complex
14
. The formation of complexes
13
and
14
is particularly interesting, as they underline the potential of complex
2
in both C-C bond formation and cleavage reactions.
We report the synthesis of a nickel(
ii
) hydroxide complex
2
supported by a rigid, tridentate triazolylidene-carbazolid ligand, acting as a versatile precursor to perform E-H (E = O, S, N) and C-H activation reactions.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>38226674</pmid><doi>10.1039/d3dt03746k</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0002-1876-2746</orcidid><orcidid>https://orcid.org/0000-0002-5353-0801</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2024-02, Vol.53 (6), p.2749-2761 |
| issn | 1477-9226 1477-9234 |
| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetonitrile Ammonium chloride Chemical synthesis Covalent bonds Dichloromethane Ligands Nickel compounds Sodium hydroxide |
| title | A mesoionic carbene stabilized nickel() hydroxide complex: a facile precursor for C-H activation chemistry |
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