Base‐Promoted Regioselective Synthesis of α‐Amino BODIPYs through Cross‐Dehydrogenative Coupling with Anilines
The construction of C−N bond at the α‐position of BODIPYs (boron dipyrromethene) not only enables flexible reactivity but also leads to strong electron‐donating properties. In this study, a base‐promoted oxidative cross‐dehydrogenative coupling was developed to synthesize α‐amino BODIPYs with air as...
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| Veröffentlicht in: | European journal of organic chemistry 2024-10, Vol.27 (40), p.n/a |
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| container_title | European journal of organic chemistry |
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| creator | Wang, Hua Guo, Luying Zuo, Huiquan Wang, Long Guo, Xing Kang, Zhengxin Li, Zhong‐Yuan Jiao, Lijuan Hao, Erhong |
| description | The construction of C−N bond at the α‐position of BODIPYs (boron dipyrromethene) not only enables flexible reactivity but also leads to strong electron‐donating properties. In this study, a base‐promoted oxidative cross‐dehydrogenative coupling was developed to synthesize α‐amino BODIPYs with air as a green oxidant. By this strategy, a series of weak nitrogen nucleophiles, such as heteroaryl and aryl anilines, were installed to the α‐position. Remarkably, pyrrole, pyrazole and indole were also employed to realize the synthesis of α‐heteroaryl BODIPYs through direct functionalization. Further aggregation‐induced emission enhancement (AIE) properties and lipid droplet‐targeting bioimaging experiments of representative dyes demonstrated their potential applications as organic probes.
A series of α‐amino BODIPYs were synthesized through a base‐promoted oxidative cross‐dehydrogenative coupling with air as a green oxidant. Furthermore, these newly synthesized BODIPYs showed potential applications as organic probes. |
| doi_str_mv | 10.1002/ejoc.202400660 |
| format | Article |
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A series of α‐amino BODIPYs were synthesized through a base‐promoted oxidative cross‐dehydrogenative coupling with air as a green oxidant. Furthermore, these newly synthesized BODIPYs showed potential applications as organic probes.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202400660</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Amino reagents ; Aniline ; Coupling ; Cross-dehydrogenative coupling ; Dehydrogenation ; Direct functionalization ; Lipids ; Medical imaging ; Nucleophiles ; Organic probes ; Oxidizing agents ; Pyrazole ; Synthesis ; α-Amino BODIPYs</subject><ispartof>European journal of organic chemistry, 2024-10, Vol.27 (40), p.n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2020-9af7a076ec97fd4194f2a27a7e9763a7a72c8800e2faaf4b75f749501504ce93</cites><orcidid>0000-0001-7234-4994</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%2Fejoc.202400660$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202400660$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Wang, Hua</creatorcontrib><creatorcontrib>Guo, Luying</creatorcontrib><creatorcontrib>Zuo, Huiquan</creatorcontrib><creatorcontrib>Wang, Long</creatorcontrib><creatorcontrib>Guo, Xing</creatorcontrib><creatorcontrib>Kang, Zhengxin</creatorcontrib><creatorcontrib>Li, Zhong‐Yuan</creatorcontrib><creatorcontrib>Jiao, Lijuan</creatorcontrib><creatorcontrib>Hao, Erhong</creatorcontrib><title>Base‐Promoted Regioselective Synthesis of α‐Amino BODIPYs through Cross‐Dehydrogenative Coupling with Anilines</title><title>European journal of organic chemistry</title><description>The construction of C−N bond at the α‐position of BODIPYs (boron dipyrromethene) not only enables flexible reactivity but also leads to strong electron‐donating properties. In this study, a base‐promoted oxidative cross‐dehydrogenative coupling was developed to synthesize α‐amino BODIPYs with air as a green oxidant. By this strategy, a series of weak nitrogen nucleophiles, such as heteroaryl and aryl anilines, were installed to the α‐position. Remarkably, pyrrole, pyrazole and indole were also employed to realize the synthesis of α‐heteroaryl BODIPYs through direct functionalization. Further aggregation‐induced emission enhancement (AIE) properties and lipid droplet‐targeting bioimaging experiments of representative dyes demonstrated their potential applications as organic probes.
A series of α‐amino BODIPYs were synthesized through a base‐promoted oxidative cross‐dehydrogenative coupling with air as a green oxidant. Furthermore, these newly synthesized BODIPYs showed potential applications as organic probes.</description><subject>Amino reagents</subject><subject>Aniline</subject><subject>Coupling</subject><subject>Cross-dehydrogenative coupling</subject><subject>Dehydrogenation</subject><subject>Direct functionalization</subject><subject>Lipids</subject><subject>Medical imaging</subject><subject>Nucleophiles</subject><subject>Organic probes</subject><subject>Oxidizing agents</subject><subject>Pyrazole</subject><subject>Synthesis</subject><subject>α-Amino BODIPYs</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFUMFOwkAUbIwmInr1vInn4ttt6bJHKKgYEohy0FOzlrd0CXRxt5Vw8xP8FX_Ej_BLXMTo0dOblzfzJjNBcE6hRQHYJS5M3mLAYoAkgYOgQUGIEBIBhx7HURxSET0cByfOLQBAJAltBHVPOvx8fZtYszIVzsgdzrVxuMS80i9I7rdlVaDTjhhFPt49s7vSpSG9cX84eXSkKqyp5wVJrXHOX_tYbGfWzLGU3_rU1OulLudko6uCdEvtF3SnwZGSS4dnP7MZTK8G0_QmHI2vh2l3FOY-B4RCKi6BJ5gLrmYxFbFiknHJUfAkkh6wvNMBQKakVPETbyseizbQNsQ5iqgZXOzfrq15rtFV2cLUtvSOWUR3DoxR7lmtPSvfZbCosrXVK2m3GYVs12y2azb7bdYLxF6w0Uvc_sPOBrfj9E_7BUiFgeo</recordid><startdate>20241021</startdate><enddate>20241021</enddate><creator>Wang, Hua</creator><creator>Guo, Luying</creator><creator>Zuo, Huiquan</creator><creator>Wang, Long</creator><creator>Guo, Xing</creator><creator>Kang, Zhengxin</creator><creator>Li, Zhong‐Yuan</creator><creator>Jiao, Lijuan</creator><creator>Hao, Erhong</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-7234-4994</orcidid></search><sort><creationdate>20241021</creationdate><title>Base‐Promoted Regioselective Synthesis of α‐Amino BODIPYs through Cross‐Dehydrogenative Coupling with Anilines</title><author>Wang, Hua ; Guo, Luying ; Zuo, Huiquan ; Wang, Long ; Guo, Xing ; Kang, Zhengxin ; Li, Zhong‐Yuan ; Jiao, Lijuan ; Hao, Erhong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2020-9af7a076ec97fd4194f2a27a7e9763a7a72c8800e2faaf4b75f749501504ce93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Amino reagents</topic><topic>Aniline</topic><topic>Coupling</topic><topic>Cross-dehydrogenative coupling</topic><topic>Dehydrogenation</topic><topic>Direct functionalization</topic><topic>Lipids</topic><topic>Medical imaging</topic><topic>Nucleophiles</topic><topic>Organic probes</topic><topic>Oxidizing agents</topic><topic>Pyrazole</topic><topic>Synthesis</topic><topic>α-Amino BODIPYs</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Hua</creatorcontrib><creatorcontrib>Guo, Luying</creatorcontrib><creatorcontrib>Zuo, Huiquan</creatorcontrib><creatorcontrib>Wang, Long</creatorcontrib><creatorcontrib>Guo, Xing</creatorcontrib><creatorcontrib>Kang, Zhengxin</creatorcontrib><creatorcontrib>Li, Zhong‐Yuan</creatorcontrib><creatorcontrib>Jiao, Lijuan</creatorcontrib><creatorcontrib>Hao, Erhong</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Hua</au><au>Guo, Luying</au><au>Zuo, Huiquan</au><au>Wang, Long</au><au>Guo, Xing</au><au>Kang, Zhengxin</au><au>Li, Zhong‐Yuan</au><au>Jiao, Lijuan</au><au>Hao, Erhong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Base‐Promoted Regioselective Synthesis of α‐Amino BODIPYs through Cross‐Dehydrogenative Coupling with Anilines</atitle><jtitle>European journal of organic chemistry</jtitle><date>2024-10-21</date><risdate>2024</risdate><volume>27</volume><issue>40</issue><epage>n/a</epage><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The construction of C−N bond at the α‐position of BODIPYs (boron dipyrromethene) not only enables flexible reactivity but also leads to strong electron‐donating properties. In this study, a base‐promoted oxidative cross‐dehydrogenative coupling was developed to synthesize α‐amino BODIPYs with air as a green oxidant. By this strategy, a series of weak nitrogen nucleophiles, such as heteroaryl and aryl anilines, were installed to the α‐position. Remarkably, pyrrole, pyrazole and indole were also employed to realize the synthesis of α‐heteroaryl BODIPYs through direct functionalization. Further aggregation‐induced emission enhancement (AIE) properties and lipid droplet‐targeting bioimaging experiments of representative dyes demonstrated their potential applications as organic probes.
A series of α‐amino BODIPYs were synthesized through a base‐promoted oxidative cross‐dehydrogenative coupling with air as a green oxidant. Furthermore, these newly synthesized BODIPYs showed potential applications as organic probes.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202400660</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0001-7234-4994</orcidid></addata></record> |
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| subjects | Amino reagents Aniline Coupling Cross-dehydrogenative coupling Dehydrogenation Direct functionalization Lipids Medical imaging Nucleophiles Organic probes Oxidizing agents Pyrazole Synthesis α-Amino BODIPYs |
| title | Base‐Promoted Regioselective Synthesis of α‐Amino BODIPYs through Cross‐Dehydrogenative Coupling with Anilines |
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