Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands
A series of imidazolium salts precursors for N -heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPr...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2019-06, Vol.48 (25), p.9317-9327 |
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| container_title | Dalton transactions : an international journal of inorganic chemistry |
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| creator | Jamil, Mohamad Shazwan Shah Alkaabi, Sultan Brisdon, Alan K |
| description | A series of imidazolium salts precursors for
N
-heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPrOH shows that the rhodium complexes bearing fluorinated NHCs are better than their non-fluorinated counterparts. The order of activity being 4-F-C
6
H
4
< 2,4-F
2
-C
6
H
3
< 2,4,5-F
3
-C
6
H
2
< 2,6-F
2
-C
6
H
3
< 2,4,6-F
3
-C
6
H
2
. This order of reactivity is consistent with a number of simple NMR measures of the electronic properties of these systems, including
1
J
CH
of the NHC·HBF
4
salts,
δ
(
77
Se) of the NHC selenides and
1
J
Rh-C
and
δ
(
13
C
carbene
) of the [Rh(cod)Cl(NHC)] complexes.
13
C and
77
Se NMR parameters for fluorinated NHC ligand precursors provide simple measures of the catalytic transfer-hydrogenation reactivity of the corresponding [Rh(cod)Cl(NHC)] complexes. |
| doi_str_mv | 10.1039/c9dt01219b |
| format | Article |
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N
-heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPrOH shows that the rhodium complexes bearing fluorinated NHCs are better than their non-fluorinated counterparts. The order of activity being 4-F-C
6
H
4
< 2,4-F
2
-C
6
H
3
< 2,4,5-F
3
-C
6
H
2
< 2,6-F
2
-C
6
H
3
< 2,4,6-F
3
-C
6
H
2
. This order of reactivity is consistent with a number of simple NMR measures of the electronic properties of these systems, including
1
J
CH
of the NHC·HBF
4
salts,
δ
(
77
Se) of the NHC selenides and
1
J
Rh-C
and
δ
(
13
C
carbene
) of the [Rh(cod)Cl(NHC)] complexes.
13
C and
77
Se NMR parameters for fluorinated NHC ligand precursors provide simple measures of the catalytic transfer-hydrogenation reactivity of the corresponding [Rh(cod)Cl(NHC)] complexes.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c9dt01219b</identifier><identifier>PMID: 31166334</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Acetophenone ; Carbenes ; Catalysis ; Catalytic activity ; Coordination compounds ; Crystallography ; Fluorination ; Hydrogenation ; NMR ; Nuclear magnetic resonance ; Rhodium ; Selenides</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2019-06, Vol.48 (25), p.9317-9327</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c373t-1afe1316a0417d0f96dc68597fff0188fd8eee8c9b1e491abfbd54aaf89f94153</citedby><cites>FETCH-LOGICAL-c373t-1afe1316a0417d0f96dc68597fff0188fd8eee8c9b1e491abfbd54aaf89f94153</cites><orcidid>0000-0002-8813-311X ; 0000-0003-1141-9344 ; 0000-0003-1909-6922</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27922,27923</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31166334$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Jamil, Mohamad Shazwan Shah</creatorcontrib><creatorcontrib>Alkaabi, Sultan</creatorcontrib><creatorcontrib>Brisdon, Alan K</creatorcontrib><title>Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>A series of imidazolium salts precursors for
N
-heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPrOH shows that the rhodium complexes bearing fluorinated NHCs are better than their non-fluorinated counterparts. The order of activity being 4-F-C
6
H
4
< 2,4-F
2
-C
6
H
3
< 2,4,5-F
3
-C
6
H
2
< 2,6-F
2
-C
6
H
3
< 2,4,6-F
3
-C
6
H
2
. This order of reactivity is consistent with a number of simple NMR measures of the electronic properties of these systems, including
1
J
CH
of the NHC·HBF
4
salts,
δ
(
77
Se) of the NHC selenides and
1
J
Rh-C
and
δ
(
13
C
carbene
) of the [Rh(cod)Cl(NHC)] complexes.
13
C and
77
Se NMR parameters for fluorinated NHC ligand precursors provide simple measures of the catalytic transfer-hydrogenation reactivity of the corresponding [Rh(cod)Cl(NHC)] complexes.</description><subject>Acetophenone</subject><subject>Carbenes</subject><subject>Catalysis</subject><subject>Catalytic activity</subject><subject>Coordination compounds</subject><subject>Crystallography</subject><subject>Fluorination</subject><subject>Hydrogenation</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Rhodium</subject><subject>Selenides</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpd0V1rFDEUBuBQlLZWb7xXAr3ZCqs5SeYjl3X8qNBWqO1VkSGTnGxTZifbJCOuv95pt27Bq3PgPLwceAl5Dew9MKE-GGUzAw6q2yH7IKtqrriQz7Y7L_fIi5RuGeOcFXyX7AmAshRC7pM_P_xy1SM9P7ugq4jWmxxiosFRo7Pu19kberO2MSxw0NmHgWqT_S-f19SFSK8vbmYm2KOmn52fNEc_qQn3cb8xUYc6j9EPC-r6MUyLzmjppGjvF3qw6SV57nSf8NXjPCBXXz5fNifz0-9fvzXHp3MjKpHnoB2CgFIzCZVlTpXWlHWhKuccg7p2tkbE2qgOUCrQnetsIbV2tXJKQiEOyGyTu4rhbsSU26VPBvteDxjG1HIuS8WUlGqih__R2zDGYfruQXEoJGeTerdRJoaUIrp2Ff1Sx3ULrL1vpG3Up8uHRj5O-O1j5Ngt0W7pvwom8GYDYjLb61Ol4i-mwJDE</recordid><startdate>20190625</startdate><enddate>20190625</enddate><creator>Jamil, Mohamad Shazwan Shah</creator><creator>Alkaabi, Sultan</creator><creator>Brisdon, Alan K</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/0000-0002-8813-311X</orcidid><orcidid>https://orcid.org/0000-0003-1141-9344</orcidid><orcidid>https://orcid.org/0000-0003-1909-6922</orcidid></search><sort><creationdate>20190625</creationdate><title>Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands</title><author>Jamil, Mohamad Shazwan Shah ; Alkaabi, Sultan ; Brisdon, Alan K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c373t-1afe1316a0417d0f96dc68597fff0188fd8eee8c9b1e491abfbd54aaf89f94153</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Acetophenone</topic><topic>Carbenes</topic><topic>Catalysis</topic><topic>Catalytic activity</topic><topic>Coordination compounds</topic><topic>Crystallography</topic><topic>Fluorination</topic><topic>Hydrogenation</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Rhodium</topic><topic>Selenides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Jamil, Mohamad Shazwan Shah</creatorcontrib><creatorcontrib>Alkaabi, Sultan</creatorcontrib><creatorcontrib>Brisdon, Alan K</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>Jamil, Mohamad Shazwan Shah</au><au>Alkaabi, Sultan</au><au>Brisdon, Alan K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2019-06-25</date><risdate>2019</risdate><volume>48</volume><issue>25</issue><spage>9317</spage><epage>9327</epage><pages>9317-9327</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>A series of imidazolium salts precursors for
N
-heterocyclic carbenes (NHCs) featuring fluoroaryl substituents have been prepared along with their selenides and rhodium complexes. Tests of the catalytic activity of the [Rh(cod)Cl(NHC)] complexes in the transfer hydrogenation of acetophenone with iPrOH shows that the rhodium complexes bearing fluorinated NHCs are better than their non-fluorinated counterparts. The order of activity being 4-F-C
6
H
4
< 2,4-F
2
-C
6
H
3
< 2,4,5-F
3
-C
6
H
2
< 2,6-F
2
-C
6
H
3
< 2,4,6-F
3
-C
6
H
2
. This order of reactivity is consistent with a number of simple NMR measures of the electronic properties of these systems, including
1
J
CH
of the NHC·HBF
4
salts,
δ
(
77
Se) of the NHC selenides and
1
J
Rh-C
and
δ
(
13
C
carbene
) of the [Rh(cod)Cl(NHC)] complexes.
13
C and
77
Se NMR parameters for fluorinated NHC ligand precursors provide simple measures of the catalytic transfer-hydrogenation reactivity of the corresponding [Rh(cod)Cl(NHC)] complexes.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>31166334</pmid><doi>10.1039/c9dt01219b</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0002-8813-311X</orcidid><orcidid>https://orcid.org/0000-0003-1141-9344</orcidid><orcidid>https://orcid.org/0000-0003-1909-6922</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2019-06, Vol.48 (25), p.9317-9327 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_pubmed_primary_31166334 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetophenone Carbenes Catalysis Catalytic activity Coordination compounds Crystallography Fluorination Hydrogenation NMR Nuclear magnetic resonance Rhodium Selenides |
| title | Simple NMR predictors of catalytic hydrogenation activity for [Rh(cod)Cl(NHC)] complexes featuring fluorinated NHC ligands |
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