Divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate
Preparation of alkyl fluorides and carbonates via divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate (CF 3 SO 2 OCF 3 ) is described. The reactions performed with BTMG in THF provided alkyl fluorides in good yields, whereas those of two differe...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2023-02, Vol.21 (6), p.1235-1241 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Ran, Long-Yu Ding, Xue Yan, Xue-Ping Zhang, Cheng-Pan |
| description | Preparation of alkyl fluorides and carbonates
via
divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate (CF
3
SO
2
OCF
3
) is described. The reactions performed with BTMG in THF provided alkyl fluorides in good yields, whereas those of two different alcohols with Et
3
N in DCM formed asymmetric carbonates in moderate to excellent yields. CF
3
SO
2
OCF
3
was demonstrated to be either a "F" or a "CO" reagent in the reactions by changing the base, allowing the selective construction of alkyl fluorides and carbonates from the corresponding alcohols with high efficiency. Notably, the fluorine-containing asymmetric carbonates that are difficult to synthesize by other methods were comprehensively prepared by this method, which would have great application potential in both academic and industrial fields.
CF
3
SO
2
OCF
3
was proved to be a useful "F"/"CO" reagent in the selective preparation of alkyl fluorides and carbonates from alcohols by varying the bases. |
| doi_str_mv | 10.1039/d2ob02028a |
| format | Article |
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via
divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate (CF
3
SO
2
OCF
3
) is described. The reactions performed with BTMG in THF provided alkyl fluorides in good yields, whereas those of two different alcohols with Et
3
N in DCM formed asymmetric carbonates in moderate to excellent yields. CF
3
SO
2
OCF
3
was demonstrated to be either a "F" or a "CO" reagent in the reactions by changing the base, allowing the selective construction of alkyl fluorides and carbonates from the corresponding alcohols with high efficiency. Notably, the fluorine-containing asymmetric carbonates that are difficult to synthesize by other methods were comprehensively prepared by this method, which would have great application potential in both academic and industrial fields.
CF
3
SO
2
OCF
3
was proved to be a useful "F"/"CO" reagent in the selective preparation of alkyl fluorides and carbonates from alcohols by varying the bases.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d2ob02028a</identifier><identifier>PMID: 36633208</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Alcohols ; Asymmetry ; Carbonates ; Carbonation ; Divergence ; Fluorides ; Fluorine ; Reagents</subject><ispartof>Organic & biomolecular chemistry, 2023-02, Vol.21 (6), p.1235-1241</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c267t-8bd782b527721fb5a9f9736548674d273281bb212ffee7919b48a0f0ef1654f93</citedby><cites>FETCH-LOGICAL-c267t-8bd782b527721fb5a9f9736548674d273281bb212ffee7919b48a0f0ef1654f93</cites><orcidid>0000-0002-2803-4611</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/36633208$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Ran, Long-Yu</creatorcontrib><creatorcontrib>Ding, Xue</creatorcontrib><creatorcontrib>Yan, Xue-Ping</creatorcontrib><creatorcontrib>Zhang, Cheng-Pan</creatorcontrib><title>Divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>Preparation of alkyl fluorides and carbonates
via
divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate (CF
3
SO
2
OCF
3
) is described. The reactions performed with BTMG in THF provided alkyl fluorides in good yields, whereas those of two different alcohols with Et
3
N in DCM formed asymmetric carbonates in moderate to excellent yields. CF
3
SO
2
OCF
3
was demonstrated to be either a "F" or a "CO" reagent in the reactions by changing the base, allowing the selective construction of alkyl fluorides and carbonates from the corresponding alcohols with high efficiency. Notably, the fluorine-containing asymmetric carbonates that are difficult to synthesize by other methods were comprehensively prepared by this method, which would have great application potential in both academic and industrial fields.
CF
3
SO
2
OCF
3
was proved to be a useful "F"/"CO" reagent in the selective preparation of alkyl fluorides and carbonates from alcohols by varying the bases.</description><subject>Alcohols</subject><subject>Asymmetry</subject><subject>Carbonates</subject><subject>Carbonation</subject><subject>Divergence</subject><subject>Fluorides</subject><subject>Fluorine</subject><subject>Reagents</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpd0c9LwzAUB_AgitPpxbtS8CJCNT_aJjnOzV8w2EXPJWkT25E1M2nV_vdmP5zoKXnk8x6PfAE4Q_AGQcJvS2wlxBAzsQeOUEJpDFPC93d3DAfg2Ps5hIjTLDkEA5JlhGDIjsB8Un8o96aaNipV1ZfOfvXadNbVjWhr20SiKaNCOGm3tdWRMIWtrPHRZ91WUevqdYNdqLbqzd9aNMp3Rq-a1Qk40MJ4dbo9h-D14f5l_BRPZ4_P49E0LnBG25jJkjIsU0wpRlqmgmtOSZYmLKNJiSnBDEmJEdZaKcoRlwkTUEOlUUCakyG42sxdOvveKd_mi9oXypiwjO18jmmWQoogJ4Fe_qNz27kmbBcUTRBkCUuDut6owlnvndL50tUL4focwXyVQD7Bs7t1AqOAL7YjO7lQ5Y7-fHkA5xvgfLF7_Y2QfAOmEYzH</recordid><startdate>20230208</startdate><enddate>20230208</enddate><creator>Ran, Long-Yu</creator><creator>Ding, Xue</creator><creator>Yan, Xue-Ping</creator><creator>Zhang, Cheng-Pan</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/0000-0002-2803-4611</orcidid></search><sort><creationdate>20230208</creationdate><title>Divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate</title><author>Ran, Long-Yu ; Ding, Xue ; Yan, Xue-Ping ; Zhang, Cheng-Pan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c267t-8bd782b527721fb5a9f9736548674d273281bb212ffee7919b48a0f0ef1654f93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Alcohols</topic><topic>Asymmetry</topic><topic>Carbonates</topic><topic>Carbonation</topic><topic>Divergence</topic><topic>Fluorides</topic><topic>Fluorine</topic><topic>Reagents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ran, Long-Yu</creatorcontrib><creatorcontrib>Ding, Xue</creatorcontrib><creatorcontrib>Yan, Xue-Ping</creatorcontrib><creatorcontrib>Zhang, Cheng-Pan</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>Ran, Long-Yu</au><au>Ding, Xue</au><au>Yan, Xue-Ping</au><au>Zhang, Cheng-Pan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2023-02-08</date><risdate>2023</risdate><volume>21</volume><issue>6</issue><spage>1235</spage><epage>1241</epage><pages>1235-1241</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Preparation of alkyl fluorides and carbonates
via
divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate (CF
3
SO
2
OCF
3
) is described. The reactions performed with BTMG in THF provided alkyl fluorides in good yields, whereas those of two different alcohols with Et
3
N in DCM formed asymmetric carbonates in moderate to excellent yields. CF
3
SO
2
OCF
3
was demonstrated to be either a "F" or a "CO" reagent in the reactions by changing the base, allowing the selective construction of alkyl fluorides and carbonates from the corresponding alcohols with high efficiency. Notably, the fluorine-containing asymmetric carbonates that are difficult to synthesize by other methods were comprehensively prepared by this method, which would have great application potential in both academic and industrial fields.
CF
3
SO
2
OCF
3
was proved to be a useful "F"/"CO" reagent in the selective preparation of alkyl fluorides and carbonates from alcohols by varying the bases.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>36633208</pmid><doi>10.1039/d2ob02028a</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-2803-4611</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2023-02, Vol.21 (6), p.1235-1241 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_journals_2774108485 |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alcohols Asymmetry Carbonates Carbonation Divergence Fluorides Fluorine Reagents |
| title | Divergent dehydroxyfluorination and carbonation of alcohols with trifluoromethyl trifluoromethanesulfonate |
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