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Synthesis of Dibenzo[c,e]oxepin-5(7H)-ones from Benzyl Thioethers and Carboxylic Acids: Rhodium-Catalyzed Double CH Activation Controlled by Different Directing Groups
A rhodium(III)‐catalyzed cross‐coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (C...
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| Published in: | Angewandte Chemie 2015-04, Vol.127 (18), p.5568-5572 |
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| Main Authors: | , , , , |
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| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c2716-a51e29867177d120d9167c772ab3cdf9404b287f22a3c0ab78f99158d30efc93 |
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| cites | cdi_FETCH-LOGICAL-c2716-a51e29867177d120d9167c772ab3cdf9404b287f22a3c0ab78f99158d30efc93 |
| container_end_page | 5572 |
| container_issue | 18 |
| container_start_page | 5568 |
| container_title | Angewandte Chemie |
| container_volume | 127 |
| creator | Zhang, Xi-Sha Zhang, Yun-Fei Li, Zhao-Wei Luo, Fei-Xian Shi, Zhang-Jie |
| description | A rhodium(III)‐catalyzed cross‐coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (CC, CO). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double CH activation, the first of such examples in cross‐oxidative coupling.
Doppelkreuz: In der Rhodium(III)‐katalysierten doppelten C‐H‐Kreuzkupplung zwischen Benzylthioethern und Carbonsäuren erhöhen die beiden dirigierenden Gruppen (DGs) die Selektivität der doppelten C‐H‐Aktivierung. Eine DG wird in das Produkt eingebaut, die andere wird in situ abgespalten. |
| doi_str_mv | 10.1002/ange.201500486 |
| format | article |
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Doppelkreuz: In der Rhodium(III)‐katalysierten doppelten C‐H‐Kreuzkupplung zwischen Benzylthioethern und Carbonsäuren erhöhen die beiden dirigierenden Gruppen (DGs) die Selektivität der doppelten C‐H‐Aktivierung. Eine DG wird in das Produkt eingebaut, die andere wird in situ abgespalten.</description><identifier>ISSN: 0044-8249</identifier><identifier>EISSN: 1521-3757</identifier><identifier>DOI: 10.1002/ange.201500486</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Activation ; Aromatic compounds ; Biocompatibility ; C-H-Aktivierung ; Carbonsäuren ; Carboxylic acids ; Cleavage ; Coupling (molecular) ; Formations ; Kreuzkupplungen ; Rhodium ; Selectivity ; Synthesemethoden ; Synthesis</subject><ispartof>Angewandte Chemie, 2015-04, Vol.127 (18), p.5568-5572</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c2716-a51e29867177d120d9167c772ab3cdf9404b287f22a3c0ab78f99158d30efc93</citedby><cites>FETCH-LOGICAL-c2716-a51e29867177d120d9167c772ab3cdf9404b287f22a3c0ab78f99158d30efc93</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Zhang, Xi-Sha</creatorcontrib><creatorcontrib>Zhang, Yun-Fei</creatorcontrib><creatorcontrib>Li, Zhao-Wei</creatorcontrib><creatorcontrib>Luo, Fei-Xian</creatorcontrib><creatorcontrib>Shi, Zhang-Jie</creatorcontrib><title>Synthesis of Dibenzo[c,e]oxepin-5(7H)-ones from Benzyl Thioethers and Carboxylic Acids: Rhodium-Catalyzed Double CH Activation Controlled by Different Directing Groups</title><title>Angewandte Chemie</title><addtitle>Angew. Chem</addtitle><description>A rhodium(III)‐catalyzed cross‐coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (CC, CO). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double CH activation, the first of such examples in cross‐oxidative coupling.
Doppelkreuz: In der Rhodium(III)‐katalysierten doppelten C‐H‐Kreuzkupplung zwischen Benzylthioethern und Carbonsäuren erhöhen die beiden dirigierenden Gruppen (DGs) die Selektivität der doppelten C‐H‐Aktivierung. Eine DG wird in das Produkt eingebaut, die andere wird in situ abgespalten.</description><subject>Activation</subject><subject>Aromatic compounds</subject><subject>Biocompatibility</subject><subject>C-H-Aktivierung</subject><subject>Carbonsäuren</subject><subject>Carboxylic acids</subject><subject>Cleavage</subject><subject>Coupling (molecular)</subject><subject>Formations</subject><subject>Kreuzkupplungen</subject><subject>Rhodium</subject><subject>Selectivity</subject><subject>Synthesemethoden</subject><subject>Synthesis</subject><issn>0044-8249</issn><issn>1521-3757</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkctuEzEUQEcIJEJhy9rLIjHB9jw8ZpdOS4KoikQisUDI8niuG4Njp_YMZPo77PgJPolfwFVQxY6Vr6xzrq50suw5wXOCMX0l3TXMKSYVxmVTP8hmpKIkL1jFHmaz9FfmDS354-xJjF8wxjVlfJb9XE9u2EI0EXmNzk0H7tZ_Ui_hsz_A3ri8OmWrF7l3EJEOfofOEjBZtNkaD0kMEUnXo1aGzh8maxRaKNPH1-jD1vdm3OWtHKSdbqFH537sLKD2949fq0QN5pscjHeo9W4I3tqEdFM6QWsI4IY0BUiUu0bL4Md9fJo90tJGePb3Pck2by427Sq_fL982y4uc0UZqXNZEaC8qRlhrCcU95zUTDFGZVeoXvMSlx1tmKZUFgrLjjWac1I1fYFBK16cZKfHtfvgb0aIg9iZqMBa6cCPURCGCcGMlSyh8yOqgo8xgBb7YHYyTIJgcddE3DUR902SwI_Cd2Nh-g8tFlfLi3_d_OiaOMDh3pXhq6hZqiw-Xi3Fu7M1L6qGi3XxBxS0ong</recordid><startdate>20150427</startdate><enddate>20150427</enddate><creator>Zhang, Xi-Sha</creator><creator>Zhang, Yun-Fei</creator><creator>Li, Zhao-Wei</creator><creator>Luo, Fei-Xian</creator><creator>Shi, Zhang-Jie</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope></search><sort><creationdate>20150427</creationdate><title>Synthesis of Dibenzo[c,e]oxepin-5(7H)-ones from Benzyl Thioethers and Carboxylic Acids: Rhodium-Catalyzed Double CH Activation Controlled by Different Directing Groups</title><author>Zhang, Xi-Sha ; Zhang, Yun-Fei ; Li, Zhao-Wei ; Luo, Fei-Xian ; Shi, Zhang-Jie</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2716-a51e29867177d120d9167c772ab3cdf9404b287f22a3c0ab78f99158d30efc93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>Activation</topic><topic>Aromatic compounds</topic><topic>Biocompatibility</topic><topic>C-H-Aktivierung</topic><topic>Carbonsäuren</topic><topic>Carboxylic acids</topic><topic>Cleavage</topic><topic>Coupling (molecular)</topic><topic>Formations</topic><topic>Kreuzkupplungen</topic><topic>Rhodium</topic><topic>Selectivity</topic><topic>Synthesemethoden</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhang, Xi-Sha</creatorcontrib><creatorcontrib>Zhang, Yun-Fei</creatorcontrib><creatorcontrib>Li, Zhao-Wei</creatorcontrib><creatorcontrib>Luo, Fei-Xian</creatorcontrib><creatorcontrib>Shi, Zhang-Jie</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><jtitle>Angewandte Chemie</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhang, Xi-Sha</au><au>Zhang, Yun-Fei</au><au>Li, Zhao-Wei</au><au>Luo, Fei-Xian</au><au>Shi, Zhang-Jie</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Dibenzo[c,e]oxepin-5(7H)-ones from Benzyl Thioethers and Carboxylic Acids: Rhodium-Catalyzed Double CH Activation Controlled by Different Directing Groups</atitle><jtitle>Angewandte Chemie</jtitle><addtitle>Angew. Chem</addtitle><date>2015-04-27</date><risdate>2015</risdate><volume>127</volume><issue>18</issue><spage>5568</spage><epage>5572</epage><pages>5568-5572</pages><issn>0044-8249</issn><eissn>1521-3757</eissn><abstract>A rhodium(III)‐catalyzed cross‐coupling of benzyl thioethers and aryl carboxylic acids through the two directing groups is reported. Useful structures with diverse substituents were efficiently synthesized in one step with the cleavage of four bonds (CH, CS, OH) and the formation of two bonds (CC, CO). The formed structure is the privileged core in natural products and bioactive molecules. This work highlights the power of using two different directing groups to enhance the selectivity of a double CH activation, the first of such examples in cross‐oxidative coupling.
Doppelkreuz: In der Rhodium(III)‐katalysierten doppelten C‐H‐Kreuzkupplung zwischen Benzylthioethern und Carbonsäuren erhöhen die beiden dirigierenden Gruppen (DGs) die Selektivität der doppelten C‐H‐Aktivierung. Eine DG wird in das Produkt eingebaut, die andere wird in situ abgespalten.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ange.201500486</doi><tpages>5</tpages></addata></record> |
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| ispartof | Angewandte Chemie, 2015-04, Vol.127 (18), p.5568-5572 |
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| subjects | Activation Aromatic compounds Biocompatibility C-H-Aktivierung Carbonsäuren Carboxylic acids Cleavage Coupling (molecular) Formations Kreuzkupplungen Rhodium Selectivity Synthesemethoden Synthesis |
| title | Synthesis of Dibenzo[c,e]oxepin-5(7H)-ones from Benzyl Thioethers and Carboxylic Acids: Rhodium-Catalyzed Double CH Activation Controlled by Different Directing Groups |
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