Molecular hydrogen and water activation by transition metal frustrated Lewis pairs containing ruthenium or osmium components: catalytic hydrogenation assays
The transition metal frustrated Lewis pair compounds [(Cym)M(κ 3 S,P,N- HL1 )][SbF 6 ] (Cym = η 6 - p -MeC 6 H 4 iPr; H 2 L1 = N -( p -tolyl)- N ′-(2-diphenylphosphanoethyl)thiourea; M = Ru ( 5 ), Os ( 6 )) have been prepared from the corresponding dimer [{(Cym)MCl} 2 (μ-Cl) 2 ] and H 2 L1 by succes...
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| Veröffentlicht in: | Dalton transactions : an international journal of inorganic chemistry 2023-09, Vol.52 (37), p.13216-13228 |
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| creator | Beard, Sophie Grasa, Alejandro Viguri, Fernando Rodríguez, Ricardo López, José A Lahoz, Fernando J García-Orduña, Pilar Lamata, Pilar Carmona, Daniel |
| description | The transition metal frustrated Lewis pair compounds [(Cym)M(κ
3
S,P,N-
HL1
)][SbF
6
] (Cym = η
6
-
p
-MeC
6
H
4
iPr;
H
2
L1
=
N
-(
p
-tolyl)-
N
′-(2-diphenylphosphanoethyl)thiourea; M = Ru (
5
), Os (
6
)) have been prepared from the corresponding dimer [{(Cym)MCl}
2
(μ-Cl)
2
] and
H
2
L1
by successive chloride abstraction with NaSbF
6
and AgSbF
6
and NH deprotonation with NaHCO
3
. Complexes
5
and
6
and the previously reported phosphano-guanidino compounds [(Cym)M(κ
3
P,N,N′-
HL2
)][SbF
6
] [
H
2
L2
=
N
,
N
′-bis(
p
-tolyl)-
N
′′-(2-diphenylphosphanoethyl) guanidine; M = Ru (
7
), Os (
8
)] and pyridinyl-guanidino compounds [(Cym)M(κ
3
N,N′,N′′-
HL3
)][SbF
6
] [
H
2
L3
=
N
,
N
′-bis(
p
-tolyl)-
N
′′-(2-pyridinylmethyl) guanidine; M = Ru (
9
), Os (
10
)] heterolytically activate H
2
in a reversible manner affording the hydrido complexes [(Cym)MH(
H
2
L
)][SbF
6
] (
H
2
L
=
H
2
L1
; M = Ru (
11
), Os (
12
);
H
2
L
=
H
2
L2
; M = Ru (
13
), Os (
14
);
H
2
L
=
H
2
L3
; M = Ru (
15
), Os (
16
)). DFT calculations carried out on the hydrogenation of complex
7
support an FLP mechanism for the process. Heating
9
and
10
in methanol yields the orthometalated complexes [(Cym)M(κ
3
N,N′,C-
H
2
L3
-H
)][SbF
6
] (M = Ru (
17
), Os (
18
)). The phosphano-guanidino complex
7
activates deuterated water in a reversible fashion, resulting in the gradual deuteration of the three cymene methyl protons through sequential C(sp
3
)-H bond activation. From DFT calculations, a metal-ligand cooperative reversible mechanism that involves the O-H bond activation and the formation of an intermediate methylene cyclohexenyl complex has been proposed. Complexes
5-10
catalyse the hydrogenation of the C&z.dbd;C double bond of styrene and a range of acrylates, the C&z.dbd;O bond of acetophenone and the C&z.dbd;N bond of
N
-benzylideneaniline and quinoline. The C&z.dbd;C double bond of methyl acrylate adds to catalyst
9
, affording complex
19
in which a new ligand exhibiting a
fac
κ
3
N,N′,C coordination mode has been incorporated.
Masked transition metal frustrated Lewis pairs containing ruthenium and osmium components activate a variety of bonds of small molecules. |
| doi_str_mv | 10.1039/d3dt02339g |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2868543484</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2860619537</sourcerecordid><originalsourceid>FETCH-LOGICAL-c332t-9b114d326ef9467b779bf133aa047841e9e89c05e2ceaac3f741c00f135e2c53</originalsourceid><addsrcrecordid>eNpd0U1v1DAQBmALUdFSuHAHWeKCkBb8FTvmhlpokRZx2Xs0cSZbV4m92A5V_gs_lmy3bKWePB4_mrH0EvKGs0-cSfu5k11hQkq7fUbOuDJmZYVUz4-10KfkZc63jAnBKvGCnEqjdcW0PiN_f8YB3TRAojdzl-IWA4XQ0TsomCi44v9A8THQdqYlQcj-_jZigYH2acpLs2BH13jnM92BT5m6GAr44MOWpqncYPDTSGOiMY_7ysVxFwOGkr9QB8ucuXh33H7YBjnDnF-Rkx6GjK8fznOy-f5tc3G9Wv-6-nHxdb1yUoqysi3nqpNCY2-VNq0xtu25lABMmVpxtFhbxyoUDgGc7I3ijrGF7FuVPCcfDmN3Kf6eMJdm9NnhMEDAOOVG1JppbitpFvr-Cb2NUwrL5_aqrpRUtVrUx4NyKeacsG92yY-Q5oazZh9ZcykvN_eRXS343cPIqR2xO9L_GS3g7QGk7I6vj5nLf8Vxn18</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2868543484</pqid></control><display><type>article</type><title>Molecular hydrogen and water activation by transition metal frustrated Lewis pairs containing ruthenium or osmium components: catalytic hydrogenation assays</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Beard, Sophie ; Grasa, Alejandro ; Viguri, Fernando ; Rodríguez, Ricardo ; López, José A ; Lahoz, Fernando J ; García-Orduña, Pilar ; Lamata, Pilar ; Carmona, Daniel</creator><creatorcontrib>Beard, Sophie ; Grasa, Alejandro ; Viguri, Fernando ; Rodríguez, Ricardo ; López, José A ; Lahoz, Fernando J ; García-Orduña, Pilar ; Lamata, Pilar ; Carmona, Daniel</creatorcontrib><description>The transition metal frustrated Lewis pair compounds [(Cym)M(κ
3
S,P,N-
HL1
)][SbF
6
] (Cym = η
6
-
p
-MeC
6
H
4
iPr;
H
2
L1
=
N
-(
p
-tolyl)-
N
′-(2-diphenylphosphanoethyl)thiourea; M = Ru (
5
), Os (
6
)) have been prepared from the corresponding dimer [{(Cym)MCl}
2
(μ-Cl)
2
] and
H
2
L1
by successive chloride abstraction with NaSbF
6
and AgSbF
6
and NH deprotonation with NaHCO
3
. Complexes
5
and
6
and the previously reported phosphano-guanidino compounds [(Cym)M(κ
3
P,N,N′-
HL2
)][SbF
6
] [
H
2
L2
=
N
,
N
′-bis(
p
-tolyl)-
N
′′-(2-diphenylphosphanoethyl) guanidine; M = Ru (
7
), Os (
8
)] and pyridinyl-guanidino compounds [(Cym)M(κ
3
N,N′,N′′-
HL3
)][SbF
6
] [
H
2
L3
=
N
,
N
′-bis(
p
-tolyl)-
N
′′-(2-pyridinylmethyl) guanidine; M = Ru (
9
), Os (
10
)] heterolytically activate H
2
in a reversible manner affording the hydrido complexes [(Cym)MH(
H
2
L
)][SbF
6
] (
H
2
L
=
H
2
L1
; M = Ru (
11
), Os (
12
);
H
2
L
=
H
2
L2
; M = Ru (
13
), Os (
14
);
H
2
L
=
H
2
L3
; M = Ru (
15
), Os (
16
)). DFT calculations carried out on the hydrogenation of complex
7
support an FLP mechanism for the process. Heating
9
and
10
in methanol yields the orthometalated complexes [(Cym)M(κ
3
N,N′,C-
H
2
L3
-H
)][SbF
6
] (M = Ru (
17
), Os (
18
)). The phosphano-guanidino complex
7
activates deuterated water in a reversible fashion, resulting in the gradual deuteration of the three cymene methyl protons through sequential C(sp
3
)-H bond activation. From DFT calculations, a metal-ligand cooperative reversible mechanism that involves the O-H bond activation and the formation of an intermediate methylene cyclohexenyl complex has been proposed. Complexes
5-10
catalyse the hydrogenation of the C&z.dbd;C double bond of styrene and a range of acrylates, the C&z.dbd;O bond of acetophenone and the C&z.dbd;N bond of
N
-benzylideneaniline and quinoline. The C&z.dbd;C double bond of methyl acrylate adds to catalyst
9
, affording complex
19
in which a new ligand exhibiting a
fac
κ
3
N,N′,C coordination mode has been incorporated.
Masked transition metal frustrated Lewis pairs containing ruthenium and osmium components activate a variety of bonds of small molecules.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/d3dt02339g</identifier><identifier>PMID: 37665066</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Acetophenone ; Acrylates ; Deuteration ; Hydrogen bonds ; Hydrogenation ; Ligands ; Mathematical analysis ; Osmium ; Quinoline ; Ruthenium ; Sodium bicarbonate ; Transition metals</subject><ispartof>Dalton transactions : an international journal of inorganic chemistry, 2023-09, Vol.52 (37), p.13216-13228</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c332t-9b114d326ef9467b779bf133aa047841e9e89c05e2ceaac3f741c00f135e2c53</cites><orcidid>0000-0002-7063-1292 ; 0000-0003-4500-1974 ; 0000-0001-8054-2237 ; 0000-0001-9071-563X ; 0000-0002-8845-0174 ; 0000-0003-4196-5856</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37665066$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Beard, Sophie</creatorcontrib><creatorcontrib>Grasa, Alejandro</creatorcontrib><creatorcontrib>Viguri, Fernando</creatorcontrib><creatorcontrib>Rodríguez, Ricardo</creatorcontrib><creatorcontrib>López, José A</creatorcontrib><creatorcontrib>Lahoz, Fernando J</creatorcontrib><creatorcontrib>García-Orduña, Pilar</creatorcontrib><creatorcontrib>Lamata, Pilar</creatorcontrib><creatorcontrib>Carmona, Daniel</creatorcontrib><title>Molecular hydrogen and water activation by transition metal frustrated Lewis pairs containing ruthenium or osmium components: catalytic hydrogenation assays</title><title>Dalton transactions : an international journal of inorganic chemistry</title><addtitle>Dalton Trans</addtitle><description>The transition metal frustrated Lewis pair compounds [(Cym)M(κ
3
S,P,N-
HL1
)][SbF
6
] (Cym = η
6
-
p
-MeC
6
H
4
iPr;
H
2
L1
=
N
-(
p
-tolyl)-
N
′-(2-diphenylphosphanoethyl)thiourea; M = Ru (
5
), Os (
6
)) have been prepared from the corresponding dimer [{(Cym)MCl}
2
(μ-Cl)
2
] and
H
2
L1
by successive chloride abstraction with NaSbF
6
and AgSbF
6
and NH deprotonation with NaHCO
3
. Complexes
5
and
6
and the previously reported phosphano-guanidino compounds [(Cym)M(κ
3
P,N,N′-
HL2
)][SbF
6
] [
H
2
L2
=
N
,
N
′-bis(
p
-tolyl)-
N
′′-(2-diphenylphosphanoethyl) guanidine; M = Ru (
7
), Os (
8
)] and pyridinyl-guanidino compounds [(Cym)M(κ
3
N,N′,N′′-
HL3
)][SbF
6
] [
H
2
L3
=
N
,
N
′-bis(
p
-tolyl)-
N
′′-(2-pyridinylmethyl) guanidine; M = Ru (
9
), Os (
10
)] heterolytically activate H
2
in a reversible manner affording the hydrido complexes [(Cym)MH(
H
2
L
)][SbF
6
] (
H
2
L
=
H
2
L1
; M = Ru (
11
), Os (
12
);
H
2
L
=
H
2
L2
; M = Ru (
13
), Os (
14
);
H
2
L
=
H
2
L3
; M = Ru (
15
), Os (
16
)). DFT calculations carried out on the hydrogenation of complex
7
support an FLP mechanism for the process. Heating
9
and
10
in methanol yields the orthometalated complexes [(Cym)M(κ
3
N,N′,C-
H
2
L3
-H
)][SbF
6
] (M = Ru (
17
), Os (
18
)). The phosphano-guanidino complex
7
activates deuterated water in a reversible fashion, resulting in the gradual deuteration of the three cymene methyl protons through sequential C(sp
3
)-H bond activation. From DFT calculations, a metal-ligand cooperative reversible mechanism that involves the O-H bond activation and the formation of an intermediate methylene cyclohexenyl complex has been proposed. Complexes
5-10
catalyse the hydrogenation of the C&z.dbd;C double bond of styrene and a range of acrylates, the C&z.dbd;O bond of acetophenone and the C&z.dbd;N bond of
N
-benzylideneaniline and quinoline. The C&z.dbd;C double bond of methyl acrylate adds to catalyst
9
, affording complex
19
in which a new ligand exhibiting a
fac
κ
3
N,N′,C coordination mode has been incorporated.
Masked transition metal frustrated Lewis pairs containing ruthenium and osmium components activate a variety of bonds of small molecules.</description><subject>Acetophenone</subject><subject>Acrylates</subject><subject>Deuteration</subject><subject>Hydrogen bonds</subject><subject>Hydrogenation</subject><subject>Ligands</subject><subject>Mathematical analysis</subject><subject>Osmium</subject><subject>Quinoline</subject><subject>Ruthenium</subject><subject>Sodium bicarbonate</subject><subject>Transition metals</subject><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpd0U1v1DAQBmALUdFSuHAHWeKCkBb8FTvmhlpokRZx2Xs0cSZbV4m92A5V_gs_lmy3bKWePB4_mrH0EvKGs0-cSfu5k11hQkq7fUbOuDJmZYVUz4-10KfkZc63jAnBKvGCnEqjdcW0PiN_f8YB3TRAojdzl-IWA4XQ0TsomCi44v9A8THQdqYlQcj-_jZigYH2acpLs2BH13jnM92BT5m6GAr44MOWpqncYPDTSGOiMY_7ysVxFwOGkr9QB8ucuXh33H7YBjnDnF-Rkx6GjK8fznOy-f5tc3G9Wv-6-nHxdb1yUoqysi3nqpNCY2-VNq0xtu25lABMmVpxtFhbxyoUDgGc7I3ijrGF7FuVPCcfDmN3Kf6eMJdm9NnhMEDAOOVG1JppbitpFvr-Cb2NUwrL5_aqrpRUtVrUx4NyKeacsG92yY-Q5oazZh9ZcykvN_eRXS343cPIqR2xO9L_GS3g7QGk7I6vj5nLf8Vxn18</recordid><startdate>20230926</startdate><enddate>20230926</enddate><creator>Beard, Sophie</creator><creator>Grasa, Alejandro</creator><creator>Viguri, Fernando</creator><creator>Rodríguez, Ricardo</creator><creator>López, José A</creator><creator>Lahoz, Fernando J</creator><creator>García-Orduña, Pilar</creator><creator>Lamata, Pilar</creator><creator>Carmona, Daniel</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/0000-0002-7063-1292</orcidid><orcidid>https://orcid.org/0000-0003-4500-1974</orcidid><orcidid>https://orcid.org/0000-0001-8054-2237</orcidid><orcidid>https://orcid.org/0000-0001-9071-563X</orcidid><orcidid>https://orcid.org/0000-0002-8845-0174</orcidid><orcidid>https://orcid.org/0000-0003-4196-5856</orcidid></search><sort><creationdate>20230926</creationdate><title>Molecular hydrogen and water activation by transition metal frustrated Lewis pairs containing ruthenium or osmium components: catalytic hydrogenation assays</title><author>Beard, Sophie ; Grasa, Alejandro ; Viguri, Fernando ; Rodríguez, Ricardo ; López, José A ; Lahoz, Fernando J ; García-Orduña, Pilar ; Lamata, Pilar ; Carmona, Daniel</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c332t-9b114d326ef9467b779bf133aa047841e9e89c05e2ceaac3f741c00f135e2c53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acetophenone</topic><topic>Acrylates</topic><topic>Deuteration</topic><topic>Hydrogen bonds</topic><topic>Hydrogenation</topic><topic>Ligands</topic><topic>Mathematical analysis</topic><topic>Osmium</topic><topic>Quinoline</topic><topic>Ruthenium</topic><topic>Sodium bicarbonate</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Beard, Sophie</creatorcontrib><creatorcontrib>Grasa, Alejandro</creatorcontrib><creatorcontrib>Viguri, Fernando</creatorcontrib><creatorcontrib>Rodríguez, Ricardo</creatorcontrib><creatorcontrib>López, José A</creatorcontrib><creatorcontrib>Lahoz, Fernando J</creatorcontrib><creatorcontrib>García-Orduña, Pilar</creatorcontrib><creatorcontrib>Lamata, Pilar</creatorcontrib><creatorcontrib>Carmona, Daniel</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>Beard, Sophie</au><au>Grasa, Alejandro</au><au>Viguri, Fernando</au><au>Rodríguez, Ricardo</au><au>López, José A</au><au>Lahoz, Fernando J</au><au>García-Orduña, Pilar</au><au>Lamata, Pilar</au><au>Carmona, Daniel</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Molecular hydrogen and water activation by transition metal frustrated Lewis pairs containing ruthenium or osmium components: catalytic hydrogenation assays</atitle><jtitle>Dalton transactions : an international journal of inorganic chemistry</jtitle><addtitle>Dalton Trans</addtitle><date>2023-09-26</date><risdate>2023</risdate><volume>52</volume><issue>37</issue><spage>13216</spage><epage>13228</epage><pages>13216-13228</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>The transition metal frustrated Lewis pair compounds [(Cym)M(κ
3
S,P,N-
HL1
)][SbF
6
] (Cym = η
6
-
p
-MeC
6
H
4
iPr;
H
2
L1
=
N
-(
p
-tolyl)-
N
′-(2-diphenylphosphanoethyl)thiourea; M = Ru (
5
), Os (
6
)) have been prepared from the corresponding dimer [{(Cym)MCl}
2
(μ-Cl)
2
] and
H
2
L1
by successive chloride abstraction with NaSbF
6
and AgSbF
6
and NH deprotonation with NaHCO
3
. Complexes
5
and
6
and the previously reported phosphano-guanidino compounds [(Cym)M(κ
3
P,N,N′-
HL2
)][SbF
6
] [
H
2
L2
=
N
,
N
′-bis(
p
-tolyl)-
N
′′-(2-diphenylphosphanoethyl) guanidine; M = Ru (
7
), Os (
8
)] and pyridinyl-guanidino compounds [(Cym)M(κ
3
N,N′,N′′-
HL3
)][SbF
6
] [
H
2
L3
=
N
,
N
′-bis(
p
-tolyl)-
N
′′-(2-pyridinylmethyl) guanidine; M = Ru (
9
), Os (
10
)] heterolytically activate H
2
in a reversible manner affording the hydrido complexes [(Cym)MH(
H
2
L
)][SbF
6
] (
H
2
L
=
H
2
L1
; M = Ru (
11
), Os (
12
);
H
2
L
=
H
2
L2
; M = Ru (
13
), Os (
14
);
H
2
L
=
H
2
L3
; M = Ru (
15
), Os (
16
)). DFT calculations carried out on the hydrogenation of complex
7
support an FLP mechanism for the process. Heating
9
and
10
in methanol yields the orthometalated complexes [(Cym)M(κ
3
N,N′,C-
H
2
L3
-H
)][SbF
6
] (M = Ru (
17
), Os (
18
)). The phosphano-guanidino complex
7
activates deuterated water in a reversible fashion, resulting in the gradual deuteration of the three cymene methyl protons through sequential C(sp
3
)-H bond activation. From DFT calculations, a metal-ligand cooperative reversible mechanism that involves the O-H bond activation and the formation of an intermediate methylene cyclohexenyl complex has been proposed. Complexes
5-10
catalyse the hydrogenation of the C&z.dbd;C double bond of styrene and a range of acrylates, the C&z.dbd;O bond of acetophenone and the C&z.dbd;N bond of
N
-benzylideneaniline and quinoline. The C&z.dbd;C double bond of methyl acrylate adds to catalyst
9
, affording complex
19
in which a new ligand exhibiting a
fac
κ
3
N,N′,C coordination mode has been incorporated.
Masked transition metal frustrated Lewis pairs containing ruthenium and osmium components activate a variety of bonds of small molecules.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>37665066</pmid><doi>10.1039/d3dt02339g</doi><tpages>13</tpages><orcidid>https://orcid.org/0000-0002-7063-1292</orcidid><orcidid>https://orcid.org/0000-0003-4500-1974</orcidid><orcidid>https://orcid.org/0000-0001-8054-2237</orcidid><orcidid>https://orcid.org/0000-0001-9071-563X</orcidid><orcidid>https://orcid.org/0000-0002-8845-0174</orcidid><orcidid>https://orcid.org/0000-0003-4196-5856</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-9226 |
| ispartof | Dalton transactions : an international journal of inorganic chemistry, 2023-09, Vol.52 (37), p.13216-13228 |
| issn | 1477-9226 1477-9234 |
| language | eng |
| recordid | cdi_proquest_journals_2868543484 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Acetophenone Acrylates Deuteration Hydrogen bonds Hydrogenation Ligands Mathematical analysis Osmium Quinoline Ruthenium Sodium bicarbonate Transition metals |
| title | Molecular hydrogen and water activation by transition metal frustrated Lewis pairs containing ruthenium or osmium components: catalytic hydrogenation assays |
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