A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: catalytic olefin aziridination reactionsDedicated to Professor Kim R. Dunbar on the occasion of her 60th birthday.Electronic supplementary information (ESI) available: Experimental details, supporting figures, spectroscopic and crystallographic data. CCDC 1841806. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8dt01851k
A bromo-capped metal-metal bonded diruthenium( i , i ) complex Ru 2 (CO) 4 (PIN) 2 Br 2 ( 1 ) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with N -bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiome...
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| creator | Sengupta, Gargi Pandey, Pragati De, Subhabrata Ramapanicker, Ramesh Bera, Jitendra K |
| description | A bromo-capped metal-metal bonded diruthenium(
i
,
i
) complex Ru
2
(CO)
4
(PIN)
2
Br
2
(
1
) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with
N
-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with
1
and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating
in situ
Br
2
generation. Complex
2
, an iodide analogue of
1
, is also synthesized. The reaction of
2
with
N
-iodosuccinimide releases I
2
, which is confirmed by the starch-iodine test. The catalytic utility of
1
is examined for the bromination of phenol. Catalyst
1
, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst
1
in the presence of NBS, K
2
CO
3
and TsNH
2
.
A bromo-capped diruthenium(
i
,
i
) complex activates NBS to produce bromine
in situ
, and thus catalyses bromine-mediated olefin aziridination reactions. |
| doi_str_mv | 10.1039/c8dt01851k |
| format | Article |
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i
,
i
) complex Ru
2
(CO)
4
(PIN)
2
Br
2
(
1
) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with
N
-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with
1
and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating
in situ
Br
2
generation. Complex
2
, an iodide analogue of
1
, is also synthesized. The reaction of
2
with
N
-iodosuccinimide releases I
2
, which is confirmed by the starch-iodine test. The catalytic utility of
1
is examined for the bromination of phenol. Catalyst
1
, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst
1
in the presence of NBS, K
2
CO
3
and TsNH
2
.
A bromo-capped diruthenium(
i
,
i
) complex activates NBS to produce bromine
in situ
, and thus catalyses bromine-mediated olefin aziridination reactions.</description><identifier>ISSN: 1477-9226</identifier><identifier>EISSN: 1477-9234</identifier><identifier>DOI: 10.1039/c8dt01851k</identifier><language>eng</language><creationdate>2018-08</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>Sengupta, Gargi</creatorcontrib><creatorcontrib>Pandey, Pragati</creatorcontrib><creatorcontrib>De, Subhabrata</creatorcontrib><creatorcontrib>Ramapanicker, Ramesh</creatorcontrib><creatorcontrib>Bera, Jitendra K</creatorcontrib><title>A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: catalytic olefin aziridination reactionsDedicated to Professor Kim R. Dunbar on the occasion of her 60th birthday.Electronic supplementary information (ESI) available: Experimental details, supporting figures, spectroscopic and crystallographic data. CCDC 1841806. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8dt01851k</title><description>A bromo-capped metal-metal bonded diruthenium(
i
,
i
) complex Ru
2
(CO)
4
(PIN)
2
Br
2
(
1
) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with
N
-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with
1
and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating
in situ
Br
2
generation. Complex
2
, an iodide analogue of
1
, is also synthesized. The reaction of
2
with
N
-iodosuccinimide releases I
2
, which is confirmed by the starch-iodine test. The catalytic utility of
1
is examined for the bromination of phenol. Catalyst
1
, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst
1
in the presence of NBS, K
2
CO
3
and TsNH
2
.
A bromo-capped diruthenium(
i
,
i
) complex activates NBS to produce bromine
in situ
, and thus catalyses bromine-mediated olefin aziridination reactions.</description><issn>1477-9226</issn><issn>1477-9234</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFUU1v00AQNQgkyseFO9Jwa6XG2E6aprkVJxERUkGUe7Rej-OB9e5qdg2Yf8k_YpwgekDAaUcz7817bzZJnudZmmfTq1d6UccsX1zkn-8nJ_ns8nJyVUxnD37XxfxR8jiET1lWFNlFcXLvxzVU7Do30cp7rKEm7mOLlvrulM7pDG4mLUZkpwdtSINWXKFF0K7zrrc1NI6BLASK_WETyXAvCFaRnIWvFFu4eX27FGZUZoiywxlshKK-E1NN9ghkVHoswgprEqx4iQ7es2swBNF4Sx18SGHV20oxCEFcgtNahZHtGmiRYZ6JWkUc21oN6dqgjuysSIbee4Md2qh4EL_iujvqnq5vt2egvigyqjK4hPU3j0wHqIEaowzC-WGB40h2Dw3te8ax5w_7g3ZeJJQcQ_MQhGbcnpVvpVlL6BTKclVCvpjli2yewkbSiOjfCeM9y-0GBOfiGAvvghyNQ0CE1bvtEv78-KfJw0aZgM9-vU-SF5v1x_LNhIPeeUkmF9jdwaf_n7_813zn62b6E6io1No</recordid><startdate>20180829</startdate><enddate>20180829</enddate><creator>Sengupta, Gargi</creator><creator>Pandey, Pragati</creator><creator>De, Subhabrata</creator><creator>Ramapanicker, Ramesh</creator><creator>Bera, Jitendra K</creator><scope/></search><sort><creationdate>20180829</creationdate><title>A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: catalytic olefin aziridination reactionsDedicated to Professor Kim R. Dunbar on the occasion of her 60th birthday.Electronic supplementary information (ESI) available: Experimental details, supporting figures, spectroscopic and crystallographic data. CCDC 1841806. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8dt01851k</title><author>Sengupta, Gargi ; Pandey, Pragati ; De, Subhabrata ; Ramapanicker, Ramesh ; Bera, Jitendra K</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c8dt01851k3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sengupta, Gargi</creatorcontrib><creatorcontrib>Pandey, Pragati</creatorcontrib><creatorcontrib>De, Subhabrata</creatorcontrib><creatorcontrib>Ramapanicker, Ramesh</creatorcontrib><creatorcontrib>Bera, Jitendra K</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sengupta, Gargi</au><au>Pandey, Pragati</au><au>De, Subhabrata</au><au>Ramapanicker, Ramesh</au><au>Bera, Jitendra K</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: catalytic olefin aziridination reactionsDedicated to Professor Kim R. Dunbar on the occasion of her 60th birthday.Electronic supplementary information (ESI) available: Experimental details, supporting figures, spectroscopic and crystallographic data. CCDC 1841806. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8dt01851k</atitle><date>2018-08-29</date><risdate>2018</risdate><volume>47</volume><issue>34</issue><spage>11917</spage><epage>11924</epage><pages>11917-11924</pages><issn>1477-9226</issn><eissn>1477-9234</eissn><abstract>A bromo-capped metal-metal bonded diruthenium(
i
,
i
) complex Ru
2
(CO)
4
(PIN)
2
Br
2
(
1
) (PIN = 1-isopropyl-3-(5,7-dimethyl-1,8-naphthyrid-2-yl)imidazol-2-ylidene) generates bromine with
N
-bromosuccinimide (NBS) at room temperature. Cycloalkene and stilbene are readily brominated by stoichiometric reactions with
1
and NBS. An analysis of the dibrominated products suggests the formation of cyclic bromonium intermediates indicating
in situ
Br
2
generation. Complex
2
, an iodide analogue of
1
, is also synthesized. The reaction of
2
with
N
-iodosuccinimide releases I
2
, which is confirmed by the starch-iodine test. The catalytic utility of
1
is examined for the bromination of phenol. Catalyst
1
, in combination with NBS and base, exhibits regioselectivity towards monobrominated products. Furthermore, efficient olefin aziridination is demonstrated utilizing catalyst
1
in the presence of NBS, K
2
CO
3
and TsNH
2
.
A bromo-capped diruthenium(
i
,
i
) complex activates NBS to produce bromine
in situ
, and thus catalyses bromine-mediated olefin aziridination reactions.</abstract><doi>10.1039/c8dt01851k</doi><tpages>8</tpages></addata></record> |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | A bromo-capped diruthenium(i,i) N-heterocyclic carbene compound for in situ bromine generation with NBS: catalytic olefin aziridination reactionsDedicated to Professor Kim R. Dunbar on the occasion of her 60th birthday.Electronic supplementary information (ESI) available: Experimental details, supporting figures, spectroscopic and crystallographic data. CCDC 1841806. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c8dt01851k |
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