Palladium catalyzed 8-aminoimidazo[1,2-]pyridine (AIP) directed selective β-C(sp)-H arylation
Palladium catalyzed arylation of the inert β-C(sp 2 )-H bond of carboxylic acid derivatives is reported herein for the first time utilizing 8-aminoimidazo[1,2- a ]pyridine (AIP) as an efficacious and new inbuilt 6,5-fused bicyclic removable directing group. This protocol is scalable, exhibits high l...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2021-01, Vol.19 (2), p.36-364 |
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| container_title | Organic & biomolecular chemistry |
| container_volume | 19 |
| creator | Mondal, Biswajit Ghosh, Prasanjit Kundu, MrinalKanti Das, Tapas Kumar Das, Sajal |
| description | Palladium catalyzed arylation of the inert β-C(sp
2
)-H bond of carboxylic acid derivatives is reported herein for the first time utilizing 8-aminoimidazo[1,2-
a
]pyridine (AIP) as an efficacious and new inbuilt 6,5-fused bicyclic removable directing group. This protocol is scalable, exhibits high levels of β-site selectivity and tolerates a broad spectrum of functional groups.
An unprecedented palladium(
ii
) catalyzed selective β-C(sp
2
)-H arylation reaction using an 8-AIP (aminoimidazo[1,2-
a
]pyridine) auxiliary as a new
N
,
N
-bidentate directing group has been demonstrated. |
| doi_str_mv | 10.1039/d0ob02134b |
| format | Article |
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2
)-H bond of carboxylic acid derivatives is reported herein for the first time utilizing 8-aminoimidazo[1,2-
a
]pyridine (AIP) as an efficacious and new inbuilt 6,5-fused bicyclic removable directing group. This protocol is scalable, exhibits high levels of β-site selectivity and tolerates a broad spectrum of functional groups.
An unprecedented palladium(
ii
) catalyzed selective β-C(sp
2
)-H arylation reaction using an 8-AIP (aminoimidazo[1,2-
a
]pyridine) auxiliary as a new
N
,
N
-bidentate directing group has been demonstrated.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d0ob02134b</identifier><identifier>PMID: 33320158</identifier><language>eng</language><publisher>CAMBRIDGE: Royal Soc Chemistry</publisher><subject>Carboxylic acids ; Chemistry ; Chemistry, Organic ; Functional groups ; Hydrogen bonds ; Palladium ; Physical Sciences ; Pyridines ; Science & Technology ; Selectivity</subject><ispartof>Organic & biomolecular chemistry, 2021-01, Vol.19 (2), p.36-364</ispartof><rights>Copyright Royal Society of Chemistry 2021</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>8</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000609532200006</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c337t-ef9343d577b993bacf21552fed74de7313d7b2fc0e1716382ddf97db791fb6593</citedby><cites>FETCH-LOGICAL-c337t-ef9343d577b993bacf21552fed74de7313d7b2fc0e1716382ddf97db791fb6593</cites><orcidid>0000-0002-9816-2889 ; 0000-0002-0907-6699 ; 0000-0002-4225-5197</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27929,27930,39263</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33320158$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Mondal, Biswajit</creatorcontrib><creatorcontrib>Ghosh, Prasanjit</creatorcontrib><creatorcontrib>Kundu, MrinalKanti</creatorcontrib><creatorcontrib>Das, Tapas Kumar</creatorcontrib><creatorcontrib>Das, Sajal</creatorcontrib><title>Palladium catalyzed 8-aminoimidazo[1,2-]pyridine (AIP) directed selective β-C(sp)-H arylation</title><title>Organic & biomolecular chemistry</title><addtitle>ORG BIOMOL CHEM</addtitle><addtitle>Org Biomol Chem</addtitle><description>Palladium catalyzed arylation of the inert β-C(sp
2
)-H bond of carboxylic acid derivatives is reported herein for the first time utilizing 8-aminoimidazo[1,2-
a
]pyridine (AIP) as an efficacious and new inbuilt 6,5-fused bicyclic removable directing group. This protocol is scalable, exhibits high levels of β-site selectivity and tolerates a broad spectrum of functional groups.
An unprecedented palladium(
ii
) catalyzed selective β-C(sp
2
)-H arylation reaction using an 8-AIP (aminoimidazo[1,2-
a
]pyridine) auxiliary as a new
N
,
N
-bidentate directing group has been demonstrated.</description><subject>Carboxylic acids</subject><subject>Chemistry</subject><subject>Chemistry, Organic</subject><subject>Functional groups</subject><subject>Hydrogen bonds</subject><subject>Palladium</subject><subject>Physical Sciences</subject><subject>Pyridines</subject><subject>Science & Technology</subject><subject>Selectivity</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>HGBXW</sourceid><recordid>eNqN0s1u1DAQB3ALgWhpuXAHReKyhaaM7SSOj20KtFKl9lBOCCJ_TCRXSby1E9D2sfogPBPeblkkTpw8h9-MPH8NIa8oHFHg8oMFr4FRXugnZJcWQuRQcvl0WzPYIS9ivAGgUlTFc7LDOWdAy3qXfL9Sfa-sm4fMqEn1qzu0WZ2rwY3eDc6qO_-VHrL823IVnHUjZovj86uDzLqAZko2Yp8K9wOzX_d5s4jLg_wsU2HVq8n5cZ8861Qf8eXju0e-fPp43ZzlF5efz5vji9xwLqYcO8kLbkshtJRcK9MxWpasQysKi4JTboVmnQGkgla8ZtZ2UlgtJO10VUq-Rxabucvgb2eMUzu4aDCtNqKfY8sKAayGuioSffsPvfFzGNPv1koWJasqSOrdRpngYwzYtcvghrRXS6Fdp96ewuXJQ-onCb95HDnrAe2W_ok5gXoDfqL2XTQOR4NbBgAVyJIzBuuycdNDdo2fxym1vv__1qRfb3SIZov-3gf_DWyapd0</recordid><startdate>20210121</startdate><enddate>20210121</enddate><creator>Mondal, Biswajit</creator><creator>Ghosh, Prasanjit</creator><creator>Kundu, MrinalKanti</creator><creator>Das, Tapas Kumar</creator><creator>Das, Sajal</creator><general>Royal Soc Chemistry</general><general>Royal Society of Chemistry</general><scope>1KM</scope><scope>BLEPL</scope><scope>DTL</scope><scope>HGBXW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-9816-2889</orcidid><orcidid>https://orcid.org/0000-0002-0907-6699</orcidid><orcidid>https://orcid.org/0000-0002-4225-5197</orcidid></search><sort><creationdate>20210121</creationdate><title>Palladium catalyzed 8-aminoimidazo[1,2-]pyridine (AIP) directed selective β-C(sp)-H arylation</title><author>Mondal, Biswajit ; Ghosh, Prasanjit ; Kundu, MrinalKanti ; Das, Tapas Kumar ; Das, Sajal</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-ef9343d577b993bacf21552fed74de7313d7b2fc0e1716382ddf97db791fb6593</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Carboxylic acids</topic><topic>Chemistry</topic><topic>Chemistry, Organic</topic><topic>Functional groups</topic><topic>Hydrogen bonds</topic><topic>Palladium</topic><topic>Physical Sciences</topic><topic>Pyridines</topic><topic>Science & Technology</topic><topic>Selectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Mondal, Biswajit</creatorcontrib><creatorcontrib>Ghosh, Prasanjit</creatorcontrib><creatorcontrib>Kundu, MrinalKanti</creatorcontrib><creatorcontrib>Das, Tapas Kumar</creatorcontrib><creatorcontrib>Das, Sajal</creatorcontrib><collection>Index Chemicus</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>Web of Science - Science Citation Index Expanded - 2021</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Mondal, Biswajit</au><au>Ghosh, Prasanjit</au><au>Kundu, MrinalKanti</au><au>Das, Tapas Kumar</au><au>Das, Sajal</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium catalyzed 8-aminoimidazo[1,2-]pyridine (AIP) directed selective β-C(sp)-H arylation</atitle><jtitle>Organic & biomolecular chemistry</jtitle><stitle>ORG BIOMOL CHEM</stitle><addtitle>Org Biomol Chem</addtitle><date>2021-01-21</date><risdate>2021</risdate><volume>19</volume><issue>2</issue><spage>36</spage><epage>364</epage><pages>36-364</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Palladium catalyzed arylation of the inert β-C(sp
2
)-H bond of carboxylic acid derivatives is reported herein for the first time utilizing 8-aminoimidazo[1,2-
a
]pyridine (AIP) as an efficacious and new inbuilt 6,5-fused bicyclic removable directing group. This protocol is scalable, exhibits high levels of β-site selectivity and tolerates a broad spectrum of functional groups.
An unprecedented palladium(
ii
) catalyzed selective β-C(sp
2
)-H arylation reaction using an 8-AIP (aminoimidazo[1,2-
a
]pyridine) auxiliary as a new
N
,
N
-bidentate directing group has been demonstrated.</abstract><cop>CAMBRIDGE</cop><pub>Royal Soc Chemistry</pub><pmid>33320158</pmid><doi>10.1039/d0ob02134b</doi><orcidid>https://orcid.org/0000-0002-9816-2889</orcidid><orcidid>https://orcid.org/0000-0002-0907-6699</orcidid><orcidid>https://orcid.org/0000-0002-4225-5197</orcidid></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2021-01, Vol.19 (2), p.36-364 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Web of Science - Science Citation Index Expanded - 2021<img src="https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg" />; Alma/SFX Local Collection |
| subjects | Carboxylic acids Chemistry Chemistry, Organic Functional groups Hydrogen bonds Palladium Physical Sciences Pyridines Science & Technology Selectivity |
| title | Palladium catalyzed 8-aminoimidazo[1,2-]pyridine (AIP) directed selective β-C(sp)-H arylation |
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