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Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina
The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. Ni/SiO 2 -Al 2 O 3 was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objec...
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| Published in: | Green chemistry : an international journal and green chemistry resource : GC 2018, Vol.2 (18), p.421-4216 |
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| Main Authors: | , , , |
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| Language: | English |
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| container_end_page | 4216 |
| container_issue | 18 |
| container_start_page | 421 |
| container_title | Green chemistry : an international journal and green chemistry resource : GC |
| container_volume | 2 |
| creator | Charvieux, Aubin Giorgi, Javier B Duguet, Nicolas Métay, Estelle |
| description | The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. Ni/SiO
2
-Al
2
O
3
was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objectives of clean and sustainable chemistry, the reaction occurs under solvent-free conditions and requires only a catalytic amount of base. This protocol was next applied to a wide range of ketones and alcohols and the desired products were isolated with 18-86% yields (26 examples). The recovery and recyclability of the nickel catalyst was also investigated and it was found to be active over 5 runs without significant loss of activity. Surprisingly, the active catalyst appears to include an amorphous nickel hydroxide layer.
The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. |
| doi_str_mv | 10.1039/c8gc01958d |
| format | article |
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2
-Al
2
O
3
was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objectives of clean and sustainable chemistry, the reaction occurs under solvent-free conditions and requires only a catalytic amount of base. This protocol was next applied to a wide range of ketones and alcohols and the desired products were isolated with 18-86% yields (26 examples). The recovery and recyclability of the nickel catalyst was also investigated and it was found to be active over 5 runs without significant loss of activity. Surprisingly, the active catalyst appears to include an amorphous nickel hydroxide layer.
The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/c8gc01958d</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acetophenone ; Alcohol ; Alkylation ; Aluminum oxide ; Benzyl alcohol ; Catalysis ; Catalysts ; Chemical Sciences ; Green chemistry ; Ketones ; Nickel ; Organic chemistry ; Recovering ; Recyclability ; Silicon dioxide ; Solvents</subject><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2018, Vol.2 (18), p.421-4216</ispartof><rights>Copyright Royal Society of Chemistry 2018</rights><rights>Distributed under a Creative Commons Attribution 4.0 International License</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c266d-db209b885121ea9fa2b2168999d61b77dec1bca10e8392ae4792966fcab5a8793</citedby><cites>FETCH-LOGICAL-c266d-db209b885121ea9fa2b2168999d61b77dec1bca10e8392ae4792966fcab5a8793</cites><orcidid>0000-0002-9425-7450 ; 0000-0002-0644-4492</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>230,314,780,784,885,4024,27923,27924,27925</link.rule.ids><backlink>$$Uhttps://udl.hal.science/hal-02128541$$DView record in HAL$$Hfree_for_read</backlink></links><search><creatorcontrib>Charvieux, Aubin</creatorcontrib><creatorcontrib>Giorgi, Javier B</creatorcontrib><creatorcontrib>Duguet, Nicolas</creatorcontrib><creatorcontrib>Métay, Estelle</creatorcontrib><title>Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. Ni/SiO
2
-Al
2
O
3
was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objectives of clean and sustainable chemistry, the reaction occurs under solvent-free conditions and requires only a catalytic amount of base. This protocol was next applied to a wide range of ketones and alcohols and the desired products were isolated with 18-86% yields (26 examples). The recovery and recyclability of the nickel catalyst was also investigated and it was found to be active over 5 runs without significant loss of activity. Surprisingly, the active catalyst appears to include an amorphous nickel hydroxide layer.
The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis.</description><subject>Acetophenone</subject><subject>Alcohol</subject><subject>Alkylation</subject><subject>Aluminum oxide</subject><subject>Benzyl alcohol</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical Sciences</subject><subject>Green chemistry</subject><subject>Ketones</subject><subject>Nickel</subject><subject>Organic chemistry</subject><subject>Recovering</subject><subject>Recyclability</subject><subject>Silicon dioxide</subject><subject>Solvents</subject><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNpFkUFLw0AQhYMoWKsX70LAk0J0Z5Nsdo8StRUKHtRzmGw2Nu02G3eTQvxX_hF_k6mReprh8c1jeM_zzoHcAAnFreTvkoCIeXHgTSBiYSBoQg73O6PH3olzK0IAEhZNvOWL0VtVt0FplfKLyirZ-t9fAep1r7GtTO2b0l-r1tTK-Xnvo5ZmabTzJbao-09V7NS6kmulfdc1jbHtoA13rtKVxMGp21Q1nnpHJWqnzv7m1Ht7fHhN58HiefaU3i0CSRkrgiKnROScx0BBoSiR5hQYF0IUDPIkKZSEXCIQxUNBUUWJoIKxUmIeI09EOPWuRt8l6qyx1QZtnxmssvndIttphALlcQRbGNjLkW2s-eiUa7OV6Ww9vJdRIDFhjIVkoK5HSlrjnFXl3hZItks9S_ks_U39foAvRtg6uef-Wwl_AOcsf2c</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Charvieux, Aubin</creator><creator>Giorgi, Javier B</creator><creator>Duguet, Nicolas</creator><creator>Métay, Estelle</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7ST</scope><scope>7U6</scope><scope>8BQ</scope><scope>8FD</scope><scope>C1K</scope><scope>JG9</scope><scope>1XC</scope><scope>VOOES</scope><orcidid>https://orcid.org/0000-0002-9425-7450</orcidid><orcidid>https://orcid.org/0000-0002-0644-4492</orcidid></search><sort><creationdate>2018</creationdate><title>Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina</title><author>Charvieux, Aubin ; Giorgi, Javier B ; Duguet, Nicolas ; Métay, Estelle</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c266d-db209b885121ea9fa2b2168999d61b77dec1bca10e8392ae4792966fcab5a8793</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Acetophenone</topic><topic>Alcohol</topic><topic>Alkylation</topic><topic>Aluminum oxide</topic><topic>Benzyl alcohol</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical Sciences</topic><topic>Green chemistry</topic><topic>Ketones</topic><topic>Nickel</topic><topic>Organic chemistry</topic><topic>Recovering</topic><topic>Recyclability</topic><topic>Silicon dioxide</topic><topic>Solvents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Charvieux, Aubin</creatorcontrib><creatorcontrib>Giorgi, Javier B</creatorcontrib><creatorcontrib>Duguet, Nicolas</creatorcontrib><creatorcontrib>Métay, Estelle</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Environment Abstracts</collection><collection>Sustainability Science Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Materials Research Database</collection><collection>Hyper Article en Ligne (HAL)</collection><collection>Hyper Article en Ligne (HAL) (Open Access)</collection><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Charvieux, Aubin</au><au>Giorgi, Javier B</au><au>Duguet, Nicolas</au><au>Métay, Estelle</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2018</date><risdate>2018</risdate><volume>2</volume><issue>18</issue><spage>421</spage><epage>4216</epage><pages>421-4216</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis. Ni/SiO
2
-Al
2
O
3
was found to be the best catalyst for this transformation and the corresponding alkylated acetophenone was obtained with 93% isolated yield. Following the objectives of clean and sustainable chemistry, the reaction occurs under solvent-free conditions and requires only a catalytic amount of base. This protocol was next applied to a wide range of ketones and alcohols and the desired products were isolated with 18-86% yields (26 examples). The recovery and recyclability of the nickel catalyst was also investigated and it was found to be active over 5 runs without significant loss of activity. Surprisingly, the active catalyst appears to include an amorphous nickel hydroxide layer.
The α-alkylation of acetophenone with benzyl alcohol through borrowing hydrogen has been studied using nickel catalysis.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/c8gc01958d</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-9425-7450</orcidid><orcidid>https://orcid.org/0000-0002-0644-4492</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1463-9262 |
| ispartof | Green chemistry : an international journal and green chemistry resource : GC, 2018, Vol.2 (18), p.421-4216 |
| issn | 1463-9262 1463-9270 |
| language | eng |
| recordid | cdi_hal_primary_oai_HAL_hal_02128541v1 |
| source | Royal Society of Chemistry |
| subjects | Acetophenone Alcohol Alkylation Aluminum oxide Benzyl alcohol Catalysis Catalysts Chemical Sciences Green chemistry Ketones Nickel Organic chemistry Recovering Recyclability Silicon dioxide Solvents |
| title | Solvent-free direct α-alkylation of ketones by alcohols catalyzed by nickel supported on silica-alumina |
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