Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex
The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoich...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2021-02, Vol.363 (4), p.1105-1111 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Gualandi, Andrea Rodeghiero, Giacomo Perciaccante, Rossana Jansen, Thomas Paul Moreno‐Cabrerizo, Cristina Foucher, Charles Marchini, Marianna Ceroni, Paola Cozzi, Pier Giorgio |
| description | The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′‐di‐tert‐butyl‐2,2′‐dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2‐phenylpyridine, 2 mol %), and N,N‐diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported. |
| doi_str_mv | 10.1002/adsc.202001250 |
| format | Article |
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Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′‐di‐tert‐butyl‐2,2′‐dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2‐phenylpyridine, 2 mol %), and N,N‐diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202001250</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Alcohols ; Aldehydes ; Allyl compounds ; Allylation ; Carbonyls ; Catalysis ; Chemical reactions ; Cobalt ; Cobalt compounds ; Iridium(III) photocatalyst ; Metalla photoredox catalysis ; Organic chemistry ; Photoredox catalysis ; Reducing agents ; Substrates ; Zinc</subject><ispartof>Advanced synthesis & catalysis, 2021-02, Vol.363 (4), p.1105-1111</ispartof><rights>2020 Wiley‐VCH GmbH</rights><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4600-be04722182629f90f9f6b59055b05c7c9fe61da975efcd705d51286dc0800e9e3</citedby><cites>FETCH-LOGICAL-c4600-be04722182629f90f9f6b59055b05c7c9fe61da975efcd705d51286dc0800e9e3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.202001250$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202001250$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Gualandi, Andrea</creatorcontrib><creatorcontrib>Rodeghiero, Giacomo</creatorcontrib><creatorcontrib>Perciaccante, Rossana</creatorcontrib><creatorcontrib>Jansen, Thomas Paul</creatorcontrib><creatorcontrib>Moreno‐Cabrerizo, Cristina</creatorcontrib><creatorcontrib>Foucher, Charles</creatorcontrib><creatorcontrib>Marchini, Marianna</creatorcontrib><creatorcontrib>Ceroni, Paola</creatorcontrib><creatorcontrib>Cozzi, Pier Giorgio</creatorcontrib><title>Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex</title><title>Advanced synthesis & catalysis</title><description>The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′‐di‐tert‐butyl‐2,2′‐dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2‐phenylpyridine, 2 mol %), and N,N‐diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported.</description><subject>Alcohols</subject><subject>Aldehydes</subject><subject>Allyl compounds</subject><subject>Allylation</subject><subject>Carbonyls</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Cobalt</subject><subject>Cobalt compounds</subject><subject>Iridium(III) photocatalyst</subject><subject>Metalla photoredox catalysis</subject><subject>Organic chemistry</subject><subject>Photoredox catalysis</subject><subject>Reducing agents</subject><subject>Substrates</subject><subject>Zinc</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LAzEQhoMoWKtXzwHPWydxs5scy_pVKFhQzyGbD7olbWqSYvffu6VSj57eGXjeGXgQuiUwIQD0XpmkJxQoAKEMztCIVIQVJanE-WlmcImuUloNTM3reoRmjcrK97nTeLEMOURrwh5Pve-9yl3Y4OCGzdhlb2zCixjWIVuD2x4r3IRW-TzEeuvt_hpdOOWTvfnNMfp8fvpoXov528usmc4LXVYARWuhrCklnFZUOAFOuKplAhhrgelaC2crYpSomXXa1MAMI5RXRgMHsMI-jNHd8e42hq-dTVmuwi5uhpeSllwwUXLOB2pypHQMKUXr5DZ2axV7SUAedMmDLnnSNRTEsfDdedv_Q8vp43vz1_0BLR5teQ</recordid><startdate>20210216</startdate><enddate>20210216</enddate><creator>Gualandi, Andrea</creator><creator>Rodeghiero, Giacomo</creator><creator>Perciaccante, Rossana</creator><creator>Jansen, Thomas Paul</creator><creator>Moreno‐Cabrerizo, Cristina</creator><creator>Foucher, Charles</creator><creator>Marchini, Marianna</creator><creator>Ceroni, Paola</creator><creator>Cozzi, Pier Giorgio</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20210216</creationdate><title>Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex</title><author>Gualandi, Andrea ; Rodeghiero, Giacomo ; Perciaccante, Rossana ; Jansen, Thomas Paul ; Moreno‐Cabrerizo, Cristina ; Foucher, Charles ; Marchini, Marianna ; Ceroni, Paola ; Cozzi, Pier Giorgio</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4600-be04722182629f90f9f6b59055b05c7c9fe61da975efcd705d51286dc0800e9e3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Alcohols</topic><topic>Aldehydes</topic><topic>Allyl compounds</topic><topic>Allylation</topic><topic>Carbonyls</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Cobalt</topic><topic>Cobalt compounds</topic><topic>Iridium(III) photocatalyst</topic><topic>Metalla photoredox catalysis</topic><topic>Organic chemistry</topic><topic>Photoredox catalysis</topic><topic>Reducing agents</topic><topic>Substrates</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gualandi, Andrea</creatorcontrib><creatorcontrib>Rodeghiero, Giacomo</creatorcontrib><creatorcontrib>Perciaccante, Rossana</creatorcontrib><creatorcontrib>Jansen, Thomas Paul</creatorcontrib><creatorcontrib>Moreno‐Cabrerizo, Cristina</creatorcontrib><creatorcontrib>Foucher, Charles</creatorcontrib><creatorcontrib>Marchini, Marianna</creatorcontrib><creatorcontrib>Ceroni, Paola</creatorcontrib><creatorcontrib>Cozzi, Pier Giorgio</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gualandi, Andrea</au><au>Rodeghiero, Giacomo</au><au>Perciaccante, Rossana</au><au>Jansen, Thomas Paul</au><au>Moreno‐Cabrerizo, Cristina</au><au>Foucher, Charles</au><au>Marchini, Marianna</au><au>Ceroni, Paola</au><au>Cozzi, Pier Giorgio</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-02-16</date><risdate>2021</risdate><volume>363</volume><issue>4</issue><spage>1105</spage><epage>1111</epage><pages>1105-1111</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The preparation of homoallylic alcohols by addition of organometallic allyl compounds to carbonyls is an important strategy in organic chemistry. Allylating organometallic cobalt species can be generated employing stoichiometric quantities of Zn acting as reductant. To avoid the employment of stoichiometric amount of Zn, we have developed an allylation reaction of aromatic and aliphatic aldehydes promoted by photoredox catalysis in the presence of a cobalt complex, and we present herein a full account of our research. In the presence of the abundant CoBr2 (10 mol %), 4,4′‐di‐tert‐butyl‐2,2′‐dipyridyl (dtbbpy, 10 mol %), allyl acetate (3 equiv.), [Ir(dtbbpy)(ppy)2]PF6 (ppy=2‐phenylpyridine, 2 mol %), and N,N‐diisopropylethylamine (4 equiv.), an allylation of aldehydes is taking place, in moderate to good yields. Substrates scope, limitations, and photophysical investigations of this new process are reported.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202001250</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Alcohols Aldehydes Allyl compounds Allylation Carbonyls Catalysis Chemical reactions Cobalt Cobalt compounds Iridium(III) photocatalyst Metalla photoredox catalysis Organic chemistry Photoredox catalysis Reducing agents Substrates Zinc |
| title | Catalytic Photoredox Allylation of Aldehydes Promoted by a Cobalt Complex |
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