Palladium-Catalyzed Cs2CO3‑Promoted Arylation of Unactivated C(sp3)–H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation
PdCl2(CH3CN)2-catalyzed arylation of unactivated C(sp3)–H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient...
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| Veröffentlicht in: | Journal of organic chemistry 2015-03, Vol.80 (6), p.3176-3186 |
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| container_end_page | 3186 |
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| container_issue | 6 |
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| container_title | Journal of organic chemistry |
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| creator | Gou, Quan Zhang, Zhao-Fu Liu, Zhi-Cheng Qin, Jun |
| description | PdCl2(CH3CN)2-catalyzed arylation of unactivated C(sp3)–H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp3)–H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway. |
| doi_str_mv | 10.1021/acs.joc.5b00111 |
| format | Article |
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The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp3)–H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.5b00111</identifier><identifier>PMID: 25763683</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Carbonates - chemistry ; Catalysis ; Cesium - chemistry ; gamma-Aminobutyric Acid - analogs & derivatives ; gamma-Aminobutyric Acid - chemical synthesis ; gamma-Aminobutyric Acid - chemistry ; Molecular Structure ; Organometallic Compounds - chemistry ; Palladium - chemistry ; Psychotropic Drugs - chemical synthesis ; Psychotropic Drugs - chemistry</subject><ispartof>Journal of organic chemistry, 2015-03, Vol.80 (6), p.3176-3186</ispartof><rights>Copyright © 2015 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.5b00111$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.5b00111$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/25763683$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Gou, Quan</creatorcontrib><creatorcontrib>Zhang, Zhao-Fu</creatorcontrib><creatorcontrib>Liu, Zhi-Cheng</creatorcontrib><creatorcontrib>Qin, Jun</creatorcontrib><title>Palladium-Catalyzed Cs2CO3‑Promoted Arylation of Unactivated C(sp3)–H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>PdCl2(CH3CN)2-catalyzed arylation of unactivated C(sp3)–H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp3)–H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. A detailed mechanism study has been conducted to understand the reaction pathway.</description><subject>Carbonates - chemistry</subject><subject>Catalysis</subject><subject>Cesium - chemistry</subject><subject>gamma-Aminobutyric Acid - analogs & derivatives</subject><subject>gamma-Aminobutyric Acid - chemical synthesis</subject><subject>gamma-Aminobutyric Acid - chemistry</subject><subject>Molecular Structure</subject><subject>Organometallic Compounds - chemistry</subject><subject>Palladium - chemistry</subject><subject>Psychotropic Drugs - chemical synthesis</subject><subject>Psychotropic Drugs - chemistry</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptUU1v1DAQtSpQuxTOvSEft0JZxvbam3BbwkeRKrWi9Gx57Qn1KomX2EGEU_8C4t_wc_pLyHa36qVzGenNm_dG8wg5YTBjwNlbY-NsHexMrgAYYwdkwiSHTBUwf0YmAJxngitxRF7EuIaxpJSH5IjLhRIqFxPy79LUtXG-b7LSJFMPv9HRMvLyQtzd_rnsQhPSiCy7oTbJh5aGil63xib_02wH5TRuxOnd7d8z-j60LtLVQKcfvLGYwq_BBxdOTYctxnf06sZXybffabpB-hXvNXwatopPbtBqdKfLHb53T-HxlJfkeWXqiK_2_Zhcf_r4rTzLzi8-fymX55kRTKRMMek45HMs5haMyhlfCGULjgvHWTU3rDALbgA5SiXBClT5Cl3uwOZQWeTimEx3upsu_OgxJt34aHF8W4uhj5opJRmHAthIfb2n9qsGnd50vjHdoB_-PRLe7AhjcHod-q4dL9cM9DZNvQOt3qcp_gPWMJWZ</recordid><startdate>20150320</startdate><enddate>20150320</enddate><creator>Gou, Quan</creator><creator>Zhang, Zhao-Fu</creator><creator>Liu, Zhi-Cheng</creator><creator>Qin, Jun</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20150320</creationdate><title>Palladium-Catalyzed Cs2CO3‑Promoted Arylation of Unactivated C(sp3)–H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation</title><author>Gou, Quan ; Zhang, Zhao-Fu ; Liu, Zhi-Cheng ; Qin, Jun</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a313t-615d2084e94c0a6812736c92e7d21f4a19a72a0e2e5650c3e68bed8d0c80fce23</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Carbonates - chemistry</topic><topic>Catalysis</topic><topic>Cesium - chemistry</topic><topic>gamma-Aminobutyric Acid - analogs & derivatives</topic><topic>gamma-Aminobutyric Acid - chemical synthesis</topic><topic>gamma-Aminobutyric Acid - chemistry</topic><topic>Molecular Structure</topic><topic>Organometallic Compounds - chemistry</topic><topic>Palladium - chemistry</topic><topic>Psychotropic Drugs - chemical synthesis</topic><topic>Psychotropic Drugs - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gou, Quan</creatorcontrib><creatorcontrib>Zhang, Zhao-Fu</creatorcontrib><creatorcontrib>Liu, Zhi-Cheng</creatorcontrib><creatorcontrib>Qin, Jun</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gou, Quan</au><au>Zhang, Zhao-Fu</au><au>Liu, Zhi-Cheng</au><au>Qin, Jun</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Palladium-Catalyzed Cs2CO3‑Promoted Arylation of Unactivated C(sp3)–H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2015-03-20</date><risdate>2015</risdate><volume>80</volume><issue>6</issue><spage>3176</spage><epage>3186</epage><pages>3176-3186</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>PdCl2(CH3CN)2-catalyzed arylation of unactivated C(sp3)–H bonds using (diacetoxyiodo)arenes as arylation reagents is reported. The reactivity of (diacetoxyiodo)arenes as arylation reagents is enabled in the presence of Cs2CO3 under the reaction conditions. This arylation method is highly efficient and occurs without the use of silver salt. The reaction tolerates a broad substrate scope that was not demonstrated by other silver salt-free C(sp3)–H bond arylation conditions. The synthetic utility of the method is further illustrated in the synthesis of the psychotropic drug phenibut. 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| ispartof | Journal of organic chemistry, 2015-03, Vol.80 (6), p.3176-3186 |
| issn | 0022-3263 1520-6904 |
| language | eng |
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| source | ACS Publications; MEDLINE |
| subjects | Carbonates - chemistry Catalysis Cesium - chemistry gamma-Aminobutyric Acid - analogs & derivatives gamma-Aminobutyric Acid - chemical synthesis gamma-Aminobutyric Acid - chemistry Molecular Structure Organometallic Compounds - chemistry Palladium - chemistry Psychotropic Drugs - chemical synthesis Psychotropic Drugs - chemistry |
| title | Palladium-Catalyzed Cs2CO3‑Promoted Arylation of Unactivated C(sp3)–H Bonds by (Diacetoxyiodo)arenes: Shifting the Reactivity of (Diacetoxyiodo)arenes from Acetoxylation to Arylation |
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