Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni() β-oxodithioester-dppe]; their use as a catalyst for Chan-Lam coupling
Novel heteroleptic [Ni( ii ) β-oxodithioester-dppe] + PF 6 − complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1 , methyl-3-hydroxy-3-( p -methoxyphenyl)-2-propenedithioate L2 2 , methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3 , methyl-3-hydroxy-3-( p -chlorophenyl...
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| Veröffentlicht in: | New journal of chemistry 2020-07, Vol.44 (28), p.12143-12153 |
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| container_issue | 28 |
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| container_title | New journal of chemistry |
| container_volume | 44 |
| creator | Kumari, Kavita Kumar, Saurabh Singh, Krishna Nand Drew, Michael G. B Singh, Nanhai |
| description | Novel heteroleptic [Ni(
ii
) β-oxodithioester-dppe]
+
PF
6
−
complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1
1
, methyl-3-hydroxy-3-(
p
-methoxyphenyl)-2-propenedithioate L2
2
, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3
3
, methyl-3-hydroxy-3-(
p
-chlorophenyl)-2-propenedithioate L4
4
, methyl-3-hydroxy-3-(
p
-bromophenyl)-2-propenedithioate L5
5
and methyl-3-hydroxy-3-(
p
-cyanophenyl)-2-propenedithioate L6
6
) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible,
1
H,
13
C{
1
H},
31
P{
1
H} and
19
F{
1
H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes
2
,
3
,
4
and
5
have been determined by X-ray crystallography. The catalytic activities of
1-6
were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford
N
-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope.
Six new structurally characterized heteroleptic cationic [Ni(
ii
) β-oxodithioester-dppe]
+
PF
6
−
complexes as efficient catalysts for Chan-Lam coupling reaction affording
N
-arylated products with significant functional group tolerance. |
| doi_str_mv | 10.1039/d0nj01139h |
| format | Article |
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ii
) β-oxodithioester-dppe]
+
PF
6
−
complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1
1
, methyl-3-hydroxy-3-(
p
-methoxyphenyl)-2-propenedithioate L2
2
, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3
3
, methyl-3-hydroxy-3-(
p
-chlorophenyl)-2-propenedithioate L4
4
, methyl-3-hydroxy-3-(
p
-bromophenyl)-2-propenedithioate L5
5
and methyl-3-hydroxy-3-(
p
-cyanophenyl)-2-propenedithioate L6
6
) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible,
1
H,
13
C{
1
H},
31
P{
1
H} and
19
F{
1
H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes
2
,
3
,
4
and
5
have been determined by X-ray crystallography. The catalytic activities of
1-6
were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford
N
-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope.
Six new structurally characterized heteroleptic cationic [Ni(
ii
) β-oxodithioester-dppe]
+
PF
6
−
complexes as efficient catalysts for Chan-Lam coupling reaction affording
N
-arylated products with significant functional group tolerance.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d0nj01139h</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Amines ; Catalysts ; Cations ; Coupling ; Crystallography ; Functional groups ; Infrared analysis ; NMR spectroscopy ; Planar structures ; Spectrum analysis ; Substrates</subject><ispartof>New journal of chemistry, 2020-07, Vol.44 (28), p.12143-12153</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c307t-bd4ded98e0a2b8a6c9ec719f8d6d88c1d76c56ec6e53f5824717f1c9fdfcaa623</citedby><cites>FETCH-LOGICAL-c307t-bd4ded98e0a2b8a6c9ec719f8d6d88c1d76c56ec6e53f5824717f1c9fdfcaa623</cites><orcidid>0000-0001-9147-5463 ; 0000-0001-8687-3440 ; 0000-0002-1468-7515 ; 0000-0003-1578-5456</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></links><search><creatorcontrib>Kumari, Kavita</creatorcontrib><creatorcontrib>Kumar, Saurabh</creatorcontrib><creatorcontrib>Singh, Krishna Nand</creatorcontrib><creatorcontrib>Drew, Michael G. B</creatorcontrib><creatorcontrib>Singh, Nanhai</creatorcontrib><title>Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni() β-oxodithioester-dppe]; their use as a catalyst for Chan-Lam coupling</title><title>New journal of chemistry</title><description>Novel heteroleptic [Ni(
ii
) β-oxodithioester-dppe]
+
PF
6
−
complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1
1
, methyl-3-hydroxy-3-(
p
-methoxyphenyl)-2-propenedithioate L2
2
, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3
3
, methyl-3-hydroxy-3-(
p
-chlorophenyl)-2-propenedithioate L4
4
, methyl-3-hydroxy-3-(
p
-bromophenyl)-2-propenedithioate L5
5
and methyl-3-hydroxy-3-(
p
-cyanophenyl)-2-propenedithioate L6
6
) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible,
1
H,
13
C{
1
H},
31
P{
1
H} and
19
F{
1
H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes
2
,
3
,
4
and
5
have been determined by X-ray crystallography. The catalytic activities of
1-6
were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford
N
-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope.
Six new structurally characterized heteroleptic cationic [Ni(
ii
) β-oxodithioester-dppe]
+
PF
6
−
complexes as efficient catalysts for Chan-Lam coupling reaction affording
N
-arylated products with significant functional group tolerance.</description><subject>Amines</subject><subject>Catalysts</subject><subject>Cations</subject><subject>Coupling</subject><subject>Crystallography</subject><subject>Functional groups</subject><subject>Infrared analysis</subject><subject>NMR spectroscopy</subject><subject>Planar structures</subject><subject>Spectrum analysis</subject><subject>Substrates</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNp9kc1uEzEUhUeISoSWDXskIzYUaag9P56xukKhNK2isgBWCI1u7GvG0cR27RnR8DQ8Aw_SZ6qTINixuke63z3nSifLnjP6ltFSnClq15SxUvSPshkruchFwdnjpFlV5bSu-JPsaYxrmqCGs1n269PWjj1GEwlYRWQPAeSIwfyE0ThLnCYWf5B4O0FA4gewEEiPiXAD-tFIIvfgTriNH_AOI_l6Y16fkvvfubtzyoy9cRjTRa68x2_nJOWZQKaIBFLqzgCGbRyJdoHMe7D5EjbJbfKDsd9PsiMNQ8Rnf-Zx9uXDxef5Il9-vLyav1vmsqTNmK9UpVCJFikUqxa4FCgbJnSruGpbyVTDZc1RcqxLXbdF1bBGMym00hKAF-Vx9urg64O7ndK_3dpNwabIrqiKqhVNyetEvTlQMrgYA-rOB7OBsO0Y7XYNdO_pzfW-gUWCXxzgEOVf7l9Daf_yf_vOK10-AL_CkxA</recordid><startdate>20200728</startdate><enddate>20200728</enddate><creator>Kumari, Kavita</creator><creator>Kumar, Saurabh</creator><creator>Singh, Krishna Nand</creator><creator>Drew, Michael G. B</creator><creator>Singh, Nanhai</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0001-9147-5463</orcidid><orcidid>https://orcid.org/0000-0001-8687-3440</orcidid><orcidid>https://orcid.org/0000-0002-1468-7515</orcidid><orcidid>https://orcid.org/0000-0003-1578-5456</orcidid></search><sort><creationdate>20200728</creationdate><title>Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni() β-oxodithioester-dppe]; their use as a catalyst for Chan-Lam coupling</title><author>Kumari, Kavita ; Kumar, Saurabh ; Singh, Krishna Nand ; Drew, Michael G. B ; Singh, Nanhai</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c307t-bd4ded98e0a2b8a6c9ec719f8d6d88c1d76c56ec6e53f5824717f1c9fdfcaa623</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amines</topic><topic>Catalysts</topic><topic>Cations</topic><topic>Coupling</topic><topic>Crystallography</topic><topic>Functional groups</topic><topic>Infrared analysis</topic><topic>NMR spectroscopy</topic><topic>Planar structures</topic><topic>Spectrum analysis</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kumari, Kavita</creatorcontrib><creatorcontrib>Kumar, Saurabh</creatorcontrib><creatorcontrib>Singh, Krishna Nand</creatorcontrib><creatorcontrib>Drew, Michael G. B</creatorcontrib><creatorcontrib>Singh, Nanhai</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kumari, Kavita</au><au>Kumar, Saurabh</au><au>Singh, Krishna Nand</au><au>Drew, Michael G. B</au><au>Singh, Nanhai</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni() β-oxodithioester-dppe]; their use as a catalyst for Chan-Lam coupling</atitle><jtitle>New journal of chemistry</jtitle><date>2020-07-28</date><risdate>2020</risdate><volume>44</volume><issue>28</issue><spage>12143</spage><epage>12153</epage><pages>12143-12153</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>Novel heteroleptic [Ni(
ii
) β-oxodithioester-dppe]
+
PF
6
−
complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1
1
, methyl-3-hydroxy-3-(
p
-methoxyphenyl)-2-propenedithioate L2
2
, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3
3
, methyl-3-hydroxy-3-(
p
-chlorophenyl)-2-propenedithioate L4
4
, methyl-3-hydroxy-3-(
p
-bromophenyl)-2-propenedithioate L5
5
and methyl-3-hydroxy-3-(
p
-cyanophenyl)-2-propenedithioate L6
6
) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible,
1
H,
13
C{
1
H},
31
P{
1
H} and
19
F{
1
H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes
2
,
3
,
4
and
5
have been determined by X-ray crystallography. The catalytic activities of
1-6
were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford
N
-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope.
Six new structurally characterized heteroleptic cationic [Ni(
ii
) β-oxodithioester-dppe]
+
PF
6
−
complexes as efficient catalysts for Chan-Lam coupling reaction affording
N
-arylated products with significant functional group tolerance.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d0nj01139h</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-9147-5463</orcidid><orcidid>https://orcid.org/0000-0001-8687-3440</orcidid><orcidid>https://orcid.org/0000-0002-1468-7515</orcidid><orcidid>https://orcid.org/0000-0003-1578-5456</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1144-0546 |
| ispartof | New journal of chemistry, 2020-07, Vol.44 (28), p.12143-12153 |
| issn | 1144-0546 1369-9261 |
| language | eng |
| recordid | cdi_rsc_primary_d0nj01139h |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amines Catalysts Cations Coupling Crystallography Functional groups Infrared analysis NMR spectroscopy Planar structures Spectrum analysis Substrates |
| title | Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni() β-oxodithioester-dppe]; their use as a catalyst for Chan-Lam coupling |
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