The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions
We have designed the first chiral diene-based metal-organic framework (MOF), E -MOF, and postsynthetically metalated E -MOF with Rh(i) complexes to afford highly active and enantioselective single-site solid catalysts for C-C bond formation reactions. Treatment of E -MOF with [RhCl(C H ) ] led to a...
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| Veröffentlicht in: | Chemical science (Cambridge) 2015-01, Vol.6 (12), p.7163-7168 |
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| creator | Sawano, Takahiro Ji, Pengfei McIsaac, Alexandra R Lin, Zekai Abney, Carter W Lin, Wenbin |
| description | We have designed the first chiral diene-based metal-organic framework (MOF), E
-MOF, and postsynthetically metalated E
-MOF with Rh(i) complexes to afford highly active and enantioselective single-site solid catalysts for C-C bond formation reactions. Treatment of E
-MOF with [RhCl(C
H
)
]
led to a highly enantioselective catalyst for 1,4-additions of arylboronic acids to α,β-unsaturated ketones, whereas treatment of E
-MOF with Rh(acac)(C
H
)
afforded a highly efficient catalyst for the asymmetric 1,2-additions of arylboronic acids to aldimines. Interestingly, E
-MOF·Rh(acac) showed higher activity and enantioselectivity than the homogeneous control catalyst, likely due to the formation of a true single-site catalyst in the MOF. E
-MOF·Rh(acac) was also successfully recycled and reused at least seven times without loss of yield and enantioselectivity. |
| doi_str_mv | 10.1039/c5sc02100f |
| format | Article |
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-MOF, and postsynthetically metalated E
-MOF with Rh(i) complexes to afford highly active and enantioselective single-site solid catalysts for C-C bond formation reactions. Treatment of E
-MOF with [RhCl(C
H
)
]
led to a highly enantioselective catalyst for 1,4-additions of arylboronic acids to α,β-unsaturated ketones, whereas treatment of E
-MOF with Rh(acac)(C
H
)
afforded a highly efficient catalyst for the asymmetric 1,2-additions of arylboronic acids to aldimines. Interestingly, E
-MOF·Rh(acac) showed higher activity and enantioselectivity than the homogeneous control catalyst, likely due to the formation of a true single-site catalyst in the MOF. E
-MOF·Rh(acac) was also successfully recycled and reused at least seven times without loss of yield and enantioselectivity.</description><identifier>ISSN: 2041-6520</identifier><identifier>ISSN: 2041-6539</identifier><identifier>EISSN: 2041-6539</identifier><identifier>DOI: 10.1039/c5sc02100f</identifier><identifier>PMID: 29861953</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Asymmetry ; Bonding ; Carbon-carbon composites ; Catalysis ; Catalysts ; Chemistry ; Ketones ; Metal-organic frameworks ; Recycled</subject><ispartof>Chemical science (Cambridge), 2015-01, Vol.6 (12), p.7163-7168</ispartof><rights>This journal is © The Royal Society of Chemistry 2015 2015</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c504t-4b77fec385199a77d1c5f2915f0da8e66662f8da0406b6eae76023c0ae7156a03</citedby><cites>FETCH-LOGICAL-c504t-4b77fec385199a77d1c5f2915f0da8e66662f8da0406b6eae76023c0ae7156a03</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5951194/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC5951194/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,723,776,780,860,881,27901,27902,53766,53768</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29861953$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink><backlink>$$Uhttps://www.osti.gov/biblio/1236871$$D View this record in Osti.gov$$Hfree_for_read</backlink></links><search><creatorcontrib>Sawano, Takahiro</creatorcontrib><creatorcontrib>Ji, Pengfei</creatorcontrib><creatorcontrib>McIsaac, Alexandra R</creatorcontrib><creatorcontrib>Lin, Zekai</creatorcontrib><creatorcontrib>Abney, Carter W</creatorcontrib><creatorcontrib>Lin, Wenbin</creatorcontrib><creatorcontrib>Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</creatorcontrib><title>The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions</title><title>Chemical science (Cambridge)</title><addtitle>Chem Sci</addtitle><description>We have designed the first chiral diene-based metal-organic framework (MOF), E
-MOF, and postsynthetically metalated E
-MOF with Rh(i) complexes to afford highly active and enantioselective single-site solid catalysts for C-C bond formation reactions. Treatment of E
-MOF with [RhCl(C
H
)
]
led to a highly enantioselective catalyst for 1,4-additions of arylboronic acids to α,β-unsaturated ketones, whereas treatment of E
-MOF with Rh(acac)(C
H
)
afforded a highly efficient catalyst for the asymmetric 1,2-additions of arylboronic acids to aldimines. Interestingly, E
-MOF·Rh(acac) showed higher activity and enantioselectivity than the homogeneous control catalyst, likely due to the formation of a true single-site catalyst in the MOF. E
-MOF·Rh(acac) was also successfully recycled and reused at least seven times without loss of yield and enantioselectivity.</description><subject>Asymmetry</subject><subject>Bonding</subject><subject>Carbon-carbon composites</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemistry</subject><subject>Ketones</subject><subject>Metal-organic frameworks</subject><subject>Recycled</subject><issn>2041-6520</issn><issn>2041-6539</issn><issn>2041-6539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkU9rFTEUxYMottRu_AASXIkwmj-TmclGkIdVoeDCug53MjdvojNJTfJa--3N66sPXXkh3AP5cZLDIeQ5Z284k_qtVdkywRlzj8ipYC1vOiX146MW7ISc5_yd1ZGSK9E_JSdCDx3XSp6SX1czUudTLtTOPsFCJ48BmxEyTnTFAksT0xaCt9QlWPE2ph-Zupjo7LfzckcxQCg-ZlzQFn-D1EIaY2gOi9Yz7fEVKhRoQrB7kZ-RJw6WjOcP-4x8u_hwtfnUXH75-Hnz_rKxirWlace-d2jloLjW0PcTt8oJzZVjEwzY1RFumIC1rBs7BOw7JqRlVXDVAZNn5N3B93o3rjhZDKWmNNfJr5DuTARv_r0JfjbbeGOUVpzrthq8PBjEXLzJ1he0s40h1LiGC9kNPa_Qq4dXUvy5w1zM6rPFZYGAcZdNLUPrlrc9-y_KB6nUIPm96-sDalPMOaE7fpszs2_fbNTXzX37FxV-8XfQI_qna_kbJL2sbQ</recordid><startdate>20150101</startdate><enddate>20150101</enddate><creator>Sawano, Takahiro</creator><creator>Ji, Pengfei</creator><creator>McIsaac, Alexandra R</creator><creator>Lin, Zekai</creator><creator>Abney, Carter W</creator><creator>Lin, Wenbin</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>7X8</scope><scope>OTOTI</scope><scope>5PM</scope></search><sort><creationdate>20150101</creationdate><title>The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions</title><author>Sawano, Takahiro ; Ji, Pengfei ; McIsaac, Alexandra R ; Lin, Zekai ; Abney, Carter W ; Lin, Wenbin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c504t-4b77fec385199a77d1c5f2915f0da8e66662f8da0406b6eae76023c0ae7156a03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Asymmetry</topic><topic>Bonding</topic><topic>Carbon-carbon composites</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemistry</topic><topic>Ketones</topic><topic>Metal-organic frameworks</topic><topic>Recycled</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sawano, Takahiro</creatorcontrib><creatorcontrib>Ji, Pengfei</creatorcontrib><creatorcontrib>McIsaac, Alexandra R</creatorcontrib><creatorcontrib>Lin, Zekai</creatorcontrib><creatorcontrib>Abney, Carter W</creatorcontrib><creatorcontrib>Lin, Wenbin</creatorcontrib><creatorcontrib>Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</creatorcontrib><collection>PubMed</collection><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>OSTI.GOV</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>Sawano, Takahiro</au><au>Ji, Pengfei</au><au>McIsaac, Alexandra R</au><au>Lin, Zekai</au><au>Abney, Carter W</au><au>Lin, Wenbin</au><aucorp>Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS)</aucorp><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions</atitle><jtitle>Chemical science (Cambridge)</jtitle><addtitle>Chem Sci</addtitle><date>2015-01-01</date><risdate>2015</risdate><volume>6</volume><issue>12</issue><spage>7163</spage><epage>7168</epage><pages>7163-7168</pages><issn>2041-6520</issn><issn>2041-6539</issn><eissn>2041-6539</eissn><abstract>We have designed the first chiral diene-based metal-organic framework (MOF), E
-MOF, and postsynthetically metalated E
-MOF with Rh(i) complexes to afford highly active and enantioselective single-site solid catalysts for C-C bond formation reactions. Treatment of E
-MOF with [RhCl(C
H
)
]
led to a highly enantioselective catalyst for 1,4-additions of arylboronic acids to α,β-unsaturated ketones, whereas treatment of E
-MOF with Rh(acac)(C
H
)
afforded a highly efficient catalyst for the asymmetric 1,2-additions of arylboronic acids to aldimines. Interestingly, E
-MOF·Rh(acac) showed higher activity and enantioselectivity than the homogeneous control catalyst, likely due to the formation of a true single-site catalyst in the MOF. E
-MOF·Rh(acac) was also successfully recycled and reused at least seven times without loss of yield and enantioselectivity.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>29861953</pmid><doi>10.1039/c5sc02100f</doi><tpages>6</tpages><oa>free_for_read</oa></addata></record> |
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| language | eng |
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| source | DOAJ Directory of Open Access Journals; EZB-FREE-00999 freely available EZB journals; PubMed Central; PubMed Central Open Access |
| subjects | Asymmetry Bonding Carbon-carbon composites Catalysis Catalysts Chemistry Ketones Metal-organic frameworks Recycled |
| title | The first chiral diene-based metal-organic frameworks for highly enantioselective carbon-carbon bond formation reactions |
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