C−H Activation Based Copper‐Catalyzed One‐Shot Synthesis of N,O‐Bidentate Organic Difluoroboron Complexes
Organic BF2 complexes exhibit characteristics such as large Stokes shift, high quantum yield, strong emission intensity, and robust chemical stability, thereby being extensively used in various applications. Herein, we disclose a novel copper‐catalyzed cascade C−H activation/acyloxylation and difluo...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2020-11, Vol.59 (48), p.21541-21545 |
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| creator | Tan, Guangying Schrader, Malte L. Daniliuc, Constantin Strieth‐Kalthoff, Felix Glorius, Frank |
| description | Organic BF2 complexes exhibit characteristics such as large Stokes shift, high quantum yield, strong emission intensity, and robust chemical stability, thereby being extensively used in various applications. Herein, we disclose a novel copper‐catalyzed cascade C−H activation/acyloxylation and difluoroboronation of 2‐phenylpyridine derivatives, thus providing a straightforward and rapid gateway to a series of N,O‐bidentate organic BF2 complexes with excellent photophysical properties. Mechanism studies demonstrate that AgBF4 services as BF2 source and oxidant for this elegant transformation. Most of these BF2 complexes have broad and intense absorption and emission bands, and display bright and intensive blue fluorescence as well as large Stokes shifts.
Don't feel blue! A novel copper‐catalyzed cascade C−H activation/acyloxylation and difluoroboronation of 2‐phenylpyridine derivatives has been developed to provide a series of N,O‐bidentate organic BF2 complexes with excellent photophysical properties. |
| doi_str_mv | 10.1002/anie.202008311 |
| format | Article |
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Don't feel blue! A novel copper‐catalyzed cascade C−H activation/acyloxylation and difluoroboronation of 2‐phenylpyridine derivatives has been developed to provide a series of N,O‐bidentate organic BF2 complexes with excellent photophysical properties.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202008311</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>blue fluorescence ; Chemical synthesis ; Copper ; copper catalysis ; C−H activation ; Emission ; Emissions ; Fluorescence ; N,O-bidentate organic BF2 complexes ; Oxidants ; Oxidizing agents</subject><ispartof>Angewandte Chemie International Edition, 2020-11, Vol.59 (48), p.21541-21545</ispartof><rights>2020 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3871-bc2d392cb667db62b22d0228df74f6833ed1dcd4f59b7fa5e5649403bb27457f3</citedby><cites>FETCH-LOGICAL-c3871-bc2d392cb667db62b22d0228df74f6833ed1dcd4f59b7fa5e5649403bb27457f3</cites><orcidid>0000-0002-0224-4784 ; 0000-0002-0648-956X ; 0000-0003-3648-8039 ; 0000-0002-6709-3673</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.202008311$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202008311$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1413,27906,27907,45556,45557</link.rule.ids></links><search><creatorcontrib>Tan, Guangying</creatorcontrib><creatorcontrib>Schrader, Malte L.</creatorcontrib><creatorcontrib>Daniliuc, Constantin</creatorcontrib><creatorcontrib>Strieth‐Kalthoff, Felix</creatorcontrib><creatorcontrib>Glorius, Frank</creatorcontrib><title>C−H Activation Based Copper‐Catalyzed One‐Shot Synthesis of N,O‐Bidentate Organic Difluoroboron Complexes</title><title>Angewandte Chemie International Edition</title><description>Organic BF2 complexes exhibit characteristics such as large Stokes shift, high quantum yield, strong emission intensity, and robust chemical stability, thereby being extensively used in various applications. Herein, we disclose a novel copper‐catalyzed cascade C−H activation/acyloxylation and difluoroboronation of 2‐phenylpyridine derivatives, thus providing a straightforward and rapid gateway to a series of N,O‐bidentate organic BF2 complexes with excellent photophysical properties. Mechanism studies demonstrate that AgBF4 services as BF2 source and oxidant for this elegant transformation. Most of these BF2 complexes have broad and intense absorption and emission bands, and display bright and intensive blue fluorescence as well as large Stokes shifts.
Don't feel blue! A novel copper‐catalyzed cascade C−H activation/acyloxylation and difluoroboronation of 2‐phenylpyridine derivatives has been developed to provide a series of N,O‐bidentate organic BF2 complexes with excellent photophysical properties.</description><subject>blue fluorescence</subject><subject>Chemical synthesis</subject><subject>Copper</subject><subject>copper catalysis</subject><subject>C−H activation</subject><subject>Emission</subject><subject>Emissions</subject><subject>Fluorescence</subject><subject>N,O-bidentate organic BF2 complexes</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkT9PwzAQxS0EElBYmSOxMJDiP4mdjiUUWgnRAZgjJz5TV2kc7BQoEyMj4iPySTAqAokFS5bPp997Ot1D6IDgPsGYnsjGQJ9iinHGCNlAOySlJGZCsM1QJ4zFIkvJNtr1fh74LMN8B93nH6_v42hYdeZBdsY20an0oKLcti24j5e3XHayXj2H1rSB8L-e2S66XjXdDLzxkdXR1fE09E-NgqaTHURTdxdGqaIzo-uldbYMtwmGi7aGJ_B7aEvL2sP-99tDt-ejm3wcX04vJvnwMq5YJkhcVlSxAa1KzoUqOS0pVZjSTGmRaJ4xBoqoSiU6HZRCyxRSngwSzMqSiiQVmvXQ0dq3dfZ-Cb4rFsZXUNeyAbv0BU0oCYcxGtDDP-jcLl0TpgsUxyLlPOyvh_prqnLWewe6aJ1ZSLcqCC6-Eii-Eih-EgiCwVrwaGpY_UMXw6vJ6Ff7CenxjeA</recordid><startdate>20201123</startdate><enddate>20201123</enddate><creator>Tan, Guangying</creator><creator>Schrader, Malte L.</creator><creator>Daniliuc, Constantin</creator><creator>Strieth‐Kalthoff, Felix</creator><creator>Glorius, Frank</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0224-4784</orcidid><orcidid>https://orcid.org/0000-0002-0648-956X</orcidid><orcidid>https://orcid.org/0000-0003-3648-8039</orcidid><orcidid>https://orcid.org/0000-0002-6709-3673</orcidid></search><sort><creationdate>20201123</creationdate><title>C−H Activation Based Copper‐Catalyzed One‐Shot Synthesis of N,O‐Bidentate Organic Difluoroboron Complexes</title><author>Tan, Guangying ; Schrader, Malte L. ; Daniliuc, Constantin ; Strieth‐Kalthoff, Felix ; Glorius, Frank</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3871-bc2d392cb667db62b22d0228df74f6833ed1dcd4f59b7fa5e5649403bb27457f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>blue fluorescence</topic><topic>Chemical synthesis</topic><topic>Copper</topic><topic>copper catalysis</topic><topic>C−H activation</topic><topic>Emission</topic><topic>Emissions</topic><topic>Fluorescence</topic><topic>N,O-bidentate organic BF2 complexes</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tan, Guangying</creatorcontrib><creatorcontrib>Schrader, Malte L.</creatorcontrib><creatorcontrib>Daniliuc, Constantin</creatorcontrib><creatorcontrib>Strieth‐Kalthoff, Felix</creatorcontrib><creatorcontrib>Glorius, Frank</creatorcontrib><collection>CrossRef</collection><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tan, Guangying</au><au>Schrader, Malte L.</au><au>Daniliuc, Constantin</au><au>Strieth‐Kalthoff, Felix</au><au>Glorius, Frank</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>C−H Activation Based Copper‐Catalyzed One‐Shot Synthesis of N,O‐Bidentate Organic Difluoroboron Complexes</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2020-11-23</date><risdate>2020</risdate><volume>59</volume><issue>48</issue><spage>21541</spage><epage>21545</epage><pages>21541-21545</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>Organic BF2 complexes exhibit characteristics such as large Stokes shift, high quantum yield, strong emission intensity, and robust chemical stability, thereby being extensively used in various applications. Herein, we disclose a novel copper‐catalyzed cascade C−H activation/acyloxylation and difluoroboronation of 2‐phenylpyridine derivatives, thus providing a straightforward and rapid gateway to a series of N,O‐bidentate organic BF2 complexes with excellent photophysical properties. Mechanism studies demonstrate that AgBF4 services as BF2 source and oxidant for this elegant transformation. Most of these BF2 complexes have broad and intense absorption and emission bands, and display bright and intensive blue fluorescence as well as large Stokes shifts.
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| subjects | blue fluorescence Chemical synthesis Copper copper catalysis C−H activation Emission Emissions Fluorescence N,O-bidentate organic BF2 complexes Oxidants Oxidizing agents |
| title | C−H Activation Based Copper‐Catalyzed One‐Shot Synthesis of N,O‐Bidentate Organic Difluoroboron Complexes |
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