Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines
Compared with the well‐known palladium‐catalyzed oxidative dehydrogenation coupling reactions, similar transforms initiated by copper/oxygen have attracted more and more attention. We have investigated a novel construction of heteroaromatic imidazo[1,2‐a]pyridines through copper(I) iodide/boron trif...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2013-09, Vol.355 (13), p.2686-2692 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Cai, Zhong-Jian Wang, Shun-Yi Ji, Shun-Jun |
| description | Compared with the well‐known palladium‐catalyzed oxidative dehydrogenation coupling reactions, similar transforms initiated by copper/oxygen have attracted more and more attention. We have investigated a novel construction of heteroaromatic imidazo[1,2‐a]pyridines through copper(I) iodide/boron trifluoride etherate/oxygen‐mediated dehydrogenative reactions of aryl alkyl or alkyl alkyl ketones with 2‐aminopyridines. Four hydrogen atoms are removed and two new CN bonds are formed in one step via the imine formation and oxidative C(sp3)H functionalization. |
| doi_str_mv | 10.1002/adsc.201300333 |
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We have investigated a novel construction of heteroaromatic imidazo[1,2‐a]pyridines through copper(I) iodide/boron trifluoride etherate/oxygen‐mediated dehydrogenative reactions of aryl alkyl or alkyl alkyl ketones with 2‐aminopyridines. Four hydrogen atoms are removed and two new CN bonds are formed in one step via the imine formation and oxidative C(sp3)H functionalization.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201300333</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>2-a]pyridines ; Boron ; C(sp3)H functionalization ; copper ; Dehydrogenation ; dehydrogenative coupling ; Hydrogen atoms ; imidazo ; imidazo[1,2‐a]pyridines ; Imines ; Iodides ; Ketones ; oxygen ; Synthesis ; Transforms</subject><ispartof>Advanced synthesis & catalysis, 2013-09, Vol.355 (13), p.2686-2692</ispartof><rights>Copyright © 2013 WILEY‐VCH Verlag GmbH & Co. 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Synth. Catal</addtitle><description>Compared with the well‐known palladium‐catalyzed oxidative dehydrogenation coupling reactions, similar transforms initiated by copper/oxygen have attracted more and more attention. We have investigated a novel construction of heteroaromatic imidazo[1,2‐a]pyridines through copper(I) iodide/boron trifluoride etherate/oxygen‐mediated dehydrogenative reactions of aryl alkyl or alkyl alkyl ketones with 2‐aminopyridines. Four hydrogen atoms are removed and two new CN bonds are formed in one step via the imine formation and oxidative C(sp3)H functionalization.</description><subject>2-a]pyridines</subject><subject>Boron</subject><subject>C(sp3)H functionalization</subject><subject>copper</subject><subject>Dehydrogenation</subject><subject>dehydrogenative coupling</subject><subject>Hydrogen atoms</subject><subject>imidazo</subject><subject>imidazo[1,2‐a]pyridines</subject><subject>Imines</subject><subject>Iodides</subject><subject>Ketones</subject><subject>oxygen</subject><subject>Synthesis</subject><subject>Transforms</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNqFkU1v1DAQhiMEEqXlytnHIpGt7ThfxyUt25VaKnWLkIqQ5Y8xNWTj1HaA9BfxM3G11YobpxnNvM-r0bxZ9obgBcGYnggd1IJiUmBcFMWz7IBUpMwZqdrn-77EL7NXIXzHmNRNXR9kfzo3juCP12_R2mmr4eS9825AN96afnI-TdBZvAMvIuSdUyKKfn4AjZbgnbQKncLdrL37BoOI9iegaxAqWjcEtBzH3ialHVAyQJt5SCXYgJxBm0mGaOMU0_4cYvIS3m2Tg0LrrdXiwX0h72guvo5zOsEOEI6yF0b0AV4_1cPs04ezm-48v7harbvlRa5YVRS5LA3olhFqJMGmNFqySoi2BCVqSVvV0kZpKZQupVLMUCKxaYSW6UtaQXreYXa88x29u58gRL61QUHfiwHcFDhhFSubklGWpIudVHkXggfDR2-3ws-cYP4YCX-MhO8jSUC7A37ZHub_qPnydNP9y-Y71oYIv_es8D94VRd1yT9_XPGGrm5vrzHml8Vfi12kcQ</recordid><startdate>20130916</startdate><enddate>20130916</enddate><creator>Cai, Zhong-Jian</creator><creator>Wang, Shun-Yi</creator><creator>Ji, Shun-Jun</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20130916</creationdate><title>Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines</title><author>Cai, Zhong-Jian ; Wang, Shun-Yi ; Ji, Shun-Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4633-b5fed9412fb10f5fdb46aa95eca7b29c928cdbacd5bcc4f21b0f8adb169dce013</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><topic>2-a]pyridines</topic><topic>Boron</topic><topic>C(sp3)H functionalization</topic><topic>copper</topic><topic>Dehydrogenation</topic><topic>dehydrogenative coupling</topic><topic>Hydrogen atoms</topic><topic>imidazo</topic><topic>imidazo[1,2‐a]pyridines</topic><topic>Imines</topic><topic>Iodides</topic><topic>Ketones</topic><topic>oxygen</topic><topic>Synthesis</topic><topic>Transforms</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Cai, Zhong-Jian</creatorcontrib><creatorcontrib>Wang, Shun-Yi</creatorcontrib><creatorcontrib>Ji, Shun-Jun</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Cai, Zhong-Jian</au><au>Wang, Shun-Yi</au><au>Ji, Shun-Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines</atitle><jtitle>Advanced synthesis & catalysis</jtitle><addtitle>Adv. Synth. Catal</addtitle><date>2013-09-16</date><risdate>2013</risdate><volume>355</volume><issue>13</issue><spage>2686</spage><epage>2692</epage><pages>2686-2692</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Compared with the well‐known palladium‐catalyzed oxidative dehydrogenation coupling reactions, similar transforms initiated by copper/oxygen have attracted more and more attention. We have investigated a novel construction of heteroaromatic imidazo[1,2‐a]pyridines through copper(I) iodide/boron trifluoride etherate/oxygen‐mediated dehydrogenative reactions of aryl alkyl or alkyl alkyl ketones with 2‐aminopyridines. Four hydrogen atoms are removed and two new CN bonds are formed in one step via the imine formation and oxidative C(sp3)H functionalization.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/adsc.201300333</doi><tpages>7</tpages></addata></record> |
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| ispartof | Advanced synthesis & catalysis, 2013-09, Vol.355 (13), p.2686-2692 |
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| source | Wiley Online Library - AutoHoldings Journals |
| subjects | 2-a]pyridines Boron C(sp3)H functionalization copper Dehydrogenation dehydrogenative coupling Hydrogen atoms imidazo imidazo[1,2‐a]pyridines Imines Iodides Ketones oxygen Synthesis Transforms |
| title | Copper(I) Iodide/Boron Trifluoride Etherate-Cocatalyzed Aerobic Dehydrogenative Reactions Applied in the Synthesis of Substituted Heteroaromatic Imidazo[1,2-a]pyridines |
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