Diverse reactivity of carbenes and silylenes towards fluoropyridines
The reaction of IDipp with C 5 F 5 N led to functionalization of all three carbon atoms of the imidazole ring with HF 2 − as the counter-anion (1). Reactivity with 2,3,5,6-tetrafluoropyridine gives only C-F bond activation leaving C-H bonds intact ( 5b ). The reaction of SIDipp with C 5 F 5 N in the...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2021-05, Vol.57 (36), p.4428-4431 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Kundu, Gargi Ajithkumar, V. S Bisai, Milan Kumar Tothadi, Srinu Das, Tamal Vanka, Kumar Sen, Sakya S |
| description | The reaction of IDipp with C
5
F
5
N led to functionalization of all three carbon atoms of the imidazole ring with HF
2
−
as the counter-anion (1). Reactivity with 2,3,5,6-tetrafluoropyridine gives only C-F bond activation leaving C-H bonds intact (
5b
). The reaction of SIDipp with C
5
F
5
N in the presence of BF
3
afforded the ring cleavage product (3). Analogous reactions with silylene led to oxidative addition at the Si(
ii
) center.
The activation of the
para
C-F bond of C
5
F
5
N by IDipp led to functionalization of all three carbon atoms of the imidazole ring. When the
para
C-F bond is replaced with a C-H bond, IDipp activates the other C-F bonds leaving the C-H bond intact. |
| doi_str_mv | 10.1039/d1cc01401c |
| format | Article |
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5
F
5
N led to functionalization of all three carbon atoms of the imidazole ring with HF
2
−
as the counter-anion (1). Reactivity with 2,3,5,6-tetrafluoropyridine gives only C-F bond activation leaving C-H bonds intact (
5b
). The reaction of SIDipp with C
5
F
5
N in the presence of BF
3
afforded the ring cleavage product (3). Analogous reactions with silylene led to oxidative addition at the Si(
ii
) center.
The activation of the
para
C-F bond of C
5
F
5
N by IDipp led to functionalization of all three carbon atoms of the imidazole ring. When the
para
C-F bond is replaced with a C-H bond, IDipp activates the other C-F bonds leaving the C-H bond intact.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d1cc01401c</identifier><identifier>PMID: 33949460</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Carbenes ; Crystallography ; Imidazole</subject><ispartof>Chemical communications (Cambridge, England), 2021-05, Vol.57 (36), p.4428-4431</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-79fe1e84c9e0b956d22beb0dee43b1574cc772dd561cee94d73a99d3904ec66c3</citedby><cites>FETCH-LOGICAL-c337t-79fe1e84c9e0b956d22beb0dee43b1574cc772dd561cee94d73a99d3904ec66c3</cites><orcidid>0000-0002-4955-5408 ; 0000-0001-7301-7573 ; 0000-0001-6840-6937</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/33949460$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kundu, Gargi</creatorcontrib><creatorcontrib>Ajithkumar, V. S</creatorcontrib><creatorcontrib>Bisai, Milan Kumar</creatorcontrib><creatorcontrib>Tothadi, Srinu</creatorcontrib><creatorcontrib>Das, Tamal</creatorcontrib><creatorcontrib>Vanka, Kumar</creatorcontrib><creatorcontrib>Sen, Sakya S</creatorcontrib><title>Diverse reactivity of carbenes and silylenes towards fluoropyridines</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>The reaction of IDipp with C
5
F
5
N led to functionalization of all three carbon atoms of the imidazole ring with HF
2
−
as the counter-anion (1). Reactivity with 2,3,5,6-tetrafluoropyridine gives only C-F bond activation leaving C-H bonds intact (
5b
). The reaction of SIDipp with C
5
F
5
N in the presence of BF
3
afforded the ring cleavage product (3). Analogous reactions with silylene led to oxidative addition at the Si(
ii
) center.
The activation of the
para
C-F bond of C
5
F
5
N by IDipp led to functionalization of all three carbon atoms of the imidazole ring. When the
para
C-F bond is replaced with a C-H bond, IDipp activates the other C-F bonds leaving the C-H bond intact.</description><subject>Carbenes</subject><subject>Crystallography</subject><subject>Imidazole</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpd0UtLxDAQB_AgiruuXrwrBS8iVJMmaZujdH3BghcFbyWdTCFLd7Mm7Uq_vd2HCuYyefwYhn8IOWf0llGu7gwDoExQBgdkzHgqYinyj8PNXqo440KOyEkIczosJvNjMuJcCSVSOibTqV2jDxh51NDatW37yNURaF_hEkOklyYKtumb7al1X9qbENVN57xb9d4aO9yfkqNaNwHP9nVC3h8f3ornePb69FLcz2LgPGvjTNXIMBegkFZKpiZJKqyoQRS8YjITAFmWGCNTBohKmIxrpQxXVCCkKfAJud71XXn32WFoy4UNgE2jl-i6UCYySbhKc8oHevWPzl3nl8N0G8VETmnOBnWzU-BdCB7rcuXtQvu-ZLTcZFtOWVFssy0GfLlv2VULNL_0J8wBXOyAD_D7-vc5_BtKFn4G</recordid><startdate>20210504</startdate><enddate>20210504</enddate><creator>Kundu, Gargi</creator><creator>Ajithkumar, V. S</creator><creator>Bisai, Milan Kumar</creator><creator>Tothadi, Srinu</creator><creator>Das, Tamal</creator><creator>Vanka, Kumar</creator><creator>Sen, Sakya S</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/0000-0002-4955-5408</orcidid><orcidid>https://orcid.org/0000-0001-7301-7573</orcidid><orcidid>https://orcid.org/0000-0001-6840-6937</orcidid></search><sort><creationdate>20210504</creationdate><title>Diverse reactivity of carbenes and silylenes towards fluoropyridines</title><author>Kundu, Gargi ; Ajithkumar, V. S ; Bisai, Milan Kumar ; Tothadi, Srinu ; Das, Tamal ; Vanka, Kumar ; Sen, Sakya S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-79fe1e84c9e0b956d22beb0dee43b1574cc772dd561cee94d73a99d3904ec66c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Carbenes</topic><topic>Crystallography</topic><topic>Imidazole</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kundu, Gargi</creatorcontrib><creatorcontrib>Ajithkumar, V. S</creatorcontrib><creatorcontrib>Bisai, Milan Kumar</creatorcontrib><creatorcontrib>Tothadi, Srinu</creatorcontrib><creatorcontrib>Das, Tamal</creatorcontrib><creatorcontrib>Vanka, Kumar</creatorcontrib><creatorcontrib>Sen, Sakya S</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>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kundu, Gargi</au><au>Ajithkumar, V. S</au><au>Bisai, Milan Kumar</au><au>Tothadi, Srinu</au><au>Das, Tamal</au><au>Vanka, Kumar</au><au>Sen, Sakya S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Diverse reactivity of carbenes and silylenes towards fluoropyridines</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2021-05-04</date><risdate>2021</risdate><volume>57</volume><issue>36</issue><spage>4428</spage><epage>4431</epage><pages>4428-4431</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>The reaction of IDipp with C
5
F
5
N led to functionalization of all three carbon atoms of the imidazole ring with HF
2
−
as the counter-anion (1). Reactivity with 2,3,5,6-tetrafluoropyridine gives only C-F bond activation leaving C-H bonds intact (
5b
). The reaction of SIDipp with C
5
F
5
N in the presence of BF
3
afforded the ring cleavage product (3). Analogous reactions with silylene led to oxidative addition at the Si(
ii
) center.
The activation of the
para
C-F bond of C
5
F
5
N by IDipp led to functionalization of all three carbon atoms of the imidazole ring. When the
para
C-F bond is replaced with a C-H bond, IDipp activates the other C-F bonds leaving the C-H bond intact.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>33949460</pmid><doi>10.1039/d1cc01401c</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-4955-5408</orcidid><orcidid>https://orcid.org/0000-0001-7301-7573</orcidid><orcidid>https://orcid.org/0000-0001-6840-6937</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2021-05, Vol.57 (36), p.4428-4431 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2522396803 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Carbenes Crystallography Imidazole |
| title | Diverse reactivity of carbenes and silylenes towards fluoropyridines |
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