B-N bond formation through palladium-catalyzed, microwave-assisted cross-coupling of nitrogen compounds with iodo-dodecaborate
Substituted undecahydrido- closo -dodecaborates [B 12 H 11 NR 2 ] 2− have potential use in materials and drugs, but have presented a synthetic challenge. Microwave-assisted palladium-catalyzed amination of iodo-dodecaborate [B 12 H 11 I] 2− allows mild and reproducible formation of B-N bonds with ar...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2021-09, Vol.57 (78), p.17-11 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Al-Joumhawy, Mahmoud K Marei, Tarek Shmalko, Akim Cendoya, Paula La Borde, Jair Gabel, Detlef |
| description | Substituted undecahydrido-
closo
-dodecaborates [B
12
H
11
NR
2
]
2−
have potential use in materials and drugs, but have presented a synthetic challenge. Microwave-assisted palladium-catalyzed amination of iodo-dodecaborate [B
12
H
11
I]
2−
allows mild and reproducible formation of B-N bonds with aromatic amines, HN-containing heteroaromatics, and amides. The reaction allows general access to amides, reproducible reactions to dodecaborate-substituted anilines, and, for the first time, the substitution of dodecaborate with HN-containing heterocycles.
A method is described which allows the synthesis of nitrogen-substituted hydridododecaborate clusters through Pd-catalyzed cross-coupling. |
| doi_str_mv | 10.1039/d1cc03215a |
| format | Article |
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closo
-dodecaborates [B
12
H
11
NR
2
]
2−
have potential use in materials and drugs, but have presented a synthetic challenge. Microwave-assisted palladium-catalyzed amination of iodo-dodecaborate [B
12
H
11
I]
2−
allows mild and reproducible formation of B-N bonds with aromatic amines, HN-containing heteroaromatics, and amides. The reaction allows general access to amides, reproducible reactions to dodecaborate-substituted anilines, and, for the first time, the substitution of dodecaborate with HN-containing heterocycles.
A method is described which allows the synthesis of nitrogen-substituted hydridododecaborate clusters through Pd-catalyzed cross-coupling.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d1cc03215a</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Amides ; Amines ; Aniline ; Coupling (molecular) ; Cross coupling ; Nitrogen compounds ; Palladium ; Substitution reactions</subject><ispartof>Chemical communications (Cambridge, England), 2021-09, Vol.57 (78), p.17-11</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c350t-a18d7629208686753885bbcdfbdd6cecdf5e979026b37021a6d89e3fa5b52063</citedby><cites>FETCH-LOGICAL-c350t-a18d7629208686753885bbcdfbdd6cecdf5e979026b37021a6d89e3fa5b52063</cites><orcidid>0000-0002-4206-282X ; 0000-0002-8003-5080</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>Al-Joumhawy, Mahmoud K</creatorcontrib><creatorcontrib>Marei, Tarek</creatorcontrib><creatorcontrib>Shmalko, Akim</creatorcontrib><creatorcontrib>Cendoya, Paula</creatorcontrib><creatorcontrib>La Borde, Jair</creatorcontrib><creatorcontrib>Gabel, Detlef</creatorcontrib><title>B-N bond formation through palladium-catalyzed, microwave-assisted cross-coupling of nitrogen compounds with iodo-dodecaborate</title><title>Chemical communications (Cambridge, England)</title><description>Substituted undecahydrido-
closo
-dodecaborates [B
12
H
11
NR
2
]
2−
have potential use in materials and drugs, but have presented a synthetic challenge. Microwave-assisted palladium-catalyzed amination of iodo-dodecaborate [B
12
H
11
I]
2−
allows mild and reproducible formation of B-N bonds with aromatic amines, HN-containing heteroaromatics, and amides. The reaction allows general access to amides, reproducible reactions to dodecaborate-substituted anilines, and, for the first time, the substitution of dodecaborate with HN-containing heterocycles.
A method is described which allows the synthesis of nitrogen-substituted hydridododecaborate clusters through Pd-catalyzed cross-coupling.</description><subject>Amides</subject><subject>Amines</subject><subject>Aniline</subject><subject>Coupling (molecular)</subject><subject>Cross coupling</subject><subject>Nitrogen compounds</subject><subject>Palladium</subject><subject>Substitution reactions</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNpdkUtLxDAUhYsoqKMb90LAjYjRPCZ9LMf6hEE3LtyVNElnMrS9NUkddOFvt3VEwbu5h8vH4R5OFB1RckEJzy41VYpwRoXcivYoj6dYTNOX7VGLDCd8Knajfe9XZBgq0r3o8wo_ohJajSpwjQwWWhSWDvrFEnWyrqW2fYOVDLJ-_zD6HDVWOVjLN4Ol99YHo9Fw8B4r6LvatgsEFWptcLAwLVLQdNC32qO1DUtkQQPWoI2SJTgZzEG0U8nam8OfPYmeb2-e83s8f7p7yGdzrLggAUua6iRmGSNpnMaJ4GkqylLpqtQ6VmYQwmRJRlhc8oQwKmOdZoZXUpSCkZhPotONbefgtTc-FI31ygzxWgO9L5gYPSkTdEBP_qEr6F07PDdSScKmCRupsw31nd2ZquicbaR7LygpxiaKa5rn303MBvh4Azuvfrm_pvgX-0yHOg</recordid><startdate>20210930</startdate><enddate>20210930</enddate><creator>Al-Joumhawy, Mahmoud K</creator><creator>Marei, Tarek</creator><creator>Shmalko, Akim</creator><creator>Cendoya, Paula</creator><creator>La Borde, Jair</creator><creator>Gabel, Detlef</creator><general>Royal Society of Chemistry</general><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/0000-0002-4206-282X</orcidid><orcidid>https://orcid.org/0000-0002-8003-5080</orcidid></search><sort><creationdate>20210930</creationdate><title>B-N bond formation through palladium-catalyzed, microwave-assisted cross-coupling of nitrogen compounds with iodo-dodecaborate</title><author>Al-Joumhawy, Mahmoud K ; Marei, Tarek ; Shmalko, Akim ; Cendoya, Paula ; La Borde, Jair ; Gabel, Detlef</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c350t-a18d7629208686753885bbcdfbdd6cecdf5e979026b37021a6d89e3fa5b52063</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Amides</topic><topic>Amines</topic><topic>Aniline</topic><topic>Coupling (molecular)</topic><topic>Cross coupling</topic><topic>Nitrogen compounds</topic><topic>Palladium</topic><topic>Substitution reactions</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Al-Joumhawy, Mahmoud K</creatorcontrib><creatorcontrib>Marei, Tarek</creatorcontrib><creatorcontrib>Shmalko, Akim</creatorcontrib><creatorcontrib>Cendoya, Paula</creatorcontrib><creatorcontrib>La Borde, Jair</creatorcontrib><creatorcontrib>Gabel, Detlef</creatorcontrib><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>Al-Joumhawy, Mahmoud K</au><au>Marei, Tarek</au><au>Shmalko, Akim</au><au>Cendoya, Paula</au><au>La Borde, Jair</au><au>Gabel, Detlef</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>B-N bond formation through palladium-catalyzed, microwave-assisted cross-coupling of nitrogen compounds with iodo-dodecaborate</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2021-09-30</date><risdate>2021</risdate><volume>57</volume><issue>78</issue><spage>17</spage><epage>11</epage><pages>17-11</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Substituted undecahydrido-
closo
-dodecaborates [B
12
H
11
NR
2
]
2−
have potential use in materials and drugs, but have presented a synthetic challenge. Microwave-assisted palladium-catalyzed amination of iodo-dodecaborate [B
12
H
11
I]
2−
allows mild and reproducible formation of B-N bonds with aromatic amines, HN-containing heteroaromatics, and amides. The reaction allows general access to amides, reproducible reactions to dodecaborate-substituted anilines, and, for the first time, the substitution of dodecaborate with HN-containing heterocycles.
A method is described which allows the synthesis of nitrogen-substituted hydridododecaborate clusters through Pd-catalyzed cross-coupling.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d1cc03215a</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-4206-282X</orcidid><orcidid>https://orcid.org/0000-0002-8003-5080</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1359-7345 |
| ispartof | Chemical communications (Cambridge, England), 2021-09, Vol.57 (78), p.17-11 |
| issn | 1359-7345 1364-548X |
| language | eng |
| recordid | cdi_proquest_journals_2577724721 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Amides Amines Aniline Coupling (molecular) Cross coupling Nitrogen compounds Palladium Substitution reactions |
| title | B-N bond formation through palladium-catalyzed, microwave-assisted cross-coupling of nitrogen compounds with iodo-dodecaborate |
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