Pyridine-catalyzed desulfonative borylation of benzyl sulfones
Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B 2 pin 2 ). A variety of benzhydryl- and benzyl boronic esters could be synthesized from readily prepared sulfone derivatives. The borylation of cyclic sulfones a...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2019-08, Vol.17 (31), p.73-733 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Maekawa, Yuuki Ariki, Zachary T Nambo, Masakazu Crudden, Cathleen M |
| description | Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B
2
pin
2
). A variety of benzhydryl- and benzyl boronic esters could be synthesized from readily prepared sulfone derivatives. The borylation of cyclic sulfones accompanied by ring opening also proceeded to afford the corresponding sulfonate, which could be converted into functionalized sulfones and sulfonamides.
Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B
2
pin
2
). |
| doi_str_mv | 10.1039/c9ob01099h |
| format | Article |
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2
pin
2
). A variety of benzhydryl- and benzyl boronic esters could be synthesized from readily prepared sulfone derivatives. The borylation of cyclic sulfones accompanied by ring opening also proceeded to afford the corresponding sulfonate, which could be converted into functionalized sulfones and sulfonamides.
Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B
2
pin
2
).</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c9ob01099h</identifier><identifier>PMID: 31338500</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Esters ; Pyridines ; Ring opening ; Sulfonamides ; Sulfones ; Transition metals</subject><ispartof>Organic & biomolecular chemistry, 2019-08, Vol.17 (31), p.73-733</ispartof><rights>Copyright Royal Society of Chemistry 2019</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c403t-64702d1f1d37d215c83ca1b4cdb8d3d53bedfc985ccb44daad48598e23f8174f3</citedby><cites>FETCH-LOGICAL-c403t-64702d1f1d37d215c83ca1b4cdb8d3d53bedfc985ccb44daad48598e23f8174f3</cites><orcidid>0000-0003-2154-8107 ; 0000-0003-0153-3178</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/31338500$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Maekawa, Yuuki</creatorcontrib><creatorcontrib>Ariki, Zachary T</creatorcontrib><creatorcontrib>Nambo, Masakazu</creatorcontrib><creatorcontrib>Crudden, Cathleen M</creatorcontrib><title>Pyridine-catalyzed desulfonative borylation of benzyl sulfones</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B
2
pin
2
). A variety of benzhydryl- and benzyl boronic esters could be synthesized from readily prepared sulfone derivatives. The borylation of cyclic sulfones accompanied by ring opening also proceeded to afford the corresponding sulfonate, which could be converted into functionalized sulfones and sulfonamides.
Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B
2
pin
2
).</description><subject>Esters</subject><subject>Pyridines</subject><subject>Ring opening</subject><subject>Sulfonamides</subject><subject>Sulfones</subject><subject>Transition metals</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNpd0U1Lw0AQBuBFFKvVi3cl4EWE6G5mk-xeBC1qhUI96DnsJ6ak2bqbCOmvNzW1gqcZmIdheAehM4JvCAZ-q7iTmGDOP_bQEaF5HuMU-P6uT_AIHYewwJjwPKOHaAQEgKUYH6G7186XuqxNrEQjqm5tdKRNaCvratGUXyaSzndV37o6cjaSpl53VTQAE07QgRVVMKfbOkbvT49vk2k8mz-_TO5nsaIYmjijOU40sURDrhOSKgZKEEmVlkyDTkEabRVnqVKSUi2EpizlzCRgGcmphTG6GvauvPtsTWiKZRmUqSpRG9eGIkkygIQC5T29_EcXrvV1f91GMc4IyVivrgelvAvBG1usfLkUvisILjapFhM-f_hJddrji-3KVi6N3tHfGHtwPgAf1G769xb4Bv12fC0</recordid><startdate>20190807</startdate><enddate>20190807</enddate><creator>Maekawa, Yuuki</creator><creator>Ariki, Zachary T</creator><creator>Nambo, Masakazu</creator><creator>Crudden, Cathleen M</creator><general>Royal Society of Chemistry</general><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/0000-0003-2154-8107</orcidid><orcidid>https://orcid.org/0000-0003-0153-3178</orcidid></search><sort><creationdate>20190807</creationdate><title>Pyridine-catalyzed desulfonative borylation of benzyl sulfones</title><author>Maekawa, Yuuki ; Ariki, Zachary T ; Nambo, Masakazu ; Crudden, Cathleen M</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c403t-64702d1f1d37d215c83ca1b4cdb8d3d53bedfc985ccb44daad48598e23f8174f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>Esters</topic><topic>Pyridines</topic><topic>Ring opening</topic><topic>Sulfonamides</topic><topic>Sulfones</topic><topic>Transition metals</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Maekawa, Yuuki</creatorcontrib><creatorcontrib>Ariki, Zachary T</creatorcontrib><creatorcontrib>Nambo, Masakazu</creatorcontrib><creatorcontrib>Crudden, Cathleen M</creatorcontrib><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>Maekawa, Yuuki</au><au>Ariki, Zachary T</au><au>Nambo, Masakazu</au><au>Crudden, Cathleen M</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Pyridine-catalyzed desulfonative borylation of benzyl sulfones</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2019-08-07</date><risdate>2019</risdate><volume>17</volume><issue>31</issue><spage>73</spage><epage>733</epage><pages>73-733</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B
2
pin
2
). A variety of benzhydryl- and benzyl boronic esters could be synthesized from readily prepared sulfone derivatives. The borylation of cyclic sulfones accompanied by ring opening also proceeded to afford the corresponding sulfonate, which could be converted into functionalized sulfones and sulfonamides.
Herein, we report the transition-metal free, pyridine-catalyzed desulfonative borylation of benzyl sulfones with bis(pinacolato)diboron (B
2
pin
2
).</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>31338500</pmid><doi>10.1039/c9ob01099h</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-2154-8107</orcidid><orcidid>https://orcid.org/0000-0003-0153-3178</orcidid></addata></record> |
| fulltext | fulltext |
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| ispartof | Organic & biomolecular chemistry, 2019-08, Vol.17 (31), p.73-733 |
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| language | eng |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Esters Pyridines Ring opening Sulfonamides Sulfones Transition metals |
| title | Pyridine-catalyzed desulfonative borylation of benzyl sulfones |
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