Synthesis of Dibenzo[g,p]chrysenes from Bis(biaryl)acetylenes via Sequential ICl-Induced Cyclization and Mizoroki−Heck Coupling
We report a facile synthesis of functionalized dibenzo[g,p]chrysenes via initial ICl-promoted cyclization of bis(biaryl)acetylenes, followed by the Mizoroki−Heck coupling reaction. This new approach works well for various bis(biaryl)acetylenes to afford dibenzo[g,p]chrysenes bearing various function...
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| Veröffentlicht in: | Journal of organic chemistry 2007-11, Vol.72 (24), p.9203-9207 |
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| container_issue | 24 |
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| container_title | Journal of organic chemistry |
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| creator | Li, Chia-Wen Wang, Cheng-I Liao, Hsin-Yi Chaudhuri, Rupsha Liu, Rai-Shung |
| description | We report a facile synthesis of functionalized dibenzo[g,p]chrysenes via initial ICl-promoted cyclization of bis(biaryl)acetylenes, followed by the Mizoroki−Heck coupling reaction. This new approach works well for various bis(biaryl)acetylenes to afford dibenzo[g,p]chrysenes bearing various functionalities. With substrates of one special type including 4‘-methoxy-2-ethynylbiphenyls, we found that the ICl treatment led to ipso cyclization to give bicyclic spirocyclohexadienones. In the presence of MeOH/H2SO4, these spiroketone products undergo rearrangement to give 9-iodophenanthrenes through a selective 1,2-alkenyl migration. We prepared various 4‘-methoxy-2-ethynylbiphenyl compounds to show the generalization of such an ipso cyclization and 1,2-alkenyl shift. This ipso-cyclization approach can be extended to the preparation of dibenzo[g,p]chrysenes. |
| doi_str_mv | 10.1021/jo701504m |
| format | Article |
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This new approach works well for various bis(biaryl)acetylenes to afford dibenzo[g,p]chrysenes bearing various functionalities. With substrates of one special type including 4‘-methoxy-2-ethynylbiphenyls, we found that the ICl treatment led to ipso cyclization to give bicyclic spirocyclohexadienones. In the presence of MeOH/H2SO4, these spiroketone products undergo rearrangement to give 9-iodophenanthrenes through a selective 1,2-alkenyl migration. We prepared various 4‘-methoxy-2-ethynylbiphenyl compounds to show the generalization of such an ipso cyclization and 1,2-alkenyl shift. 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Org. Chem</addtitle><description>We report a facile synthesis of functionalized dibenzo[g,p]chrysenes via initial ICl-promoted cyclization of bis(biaryl)acetylenes, followed by the Mizoroki−Heck coupling reaction. This new approach works well for various bis(biaryl)acetylenes to afford dibenzo[g,p]chrysenes bearing various functionalities. With substrates of one special type including 4‘-methoxy-2-ethynylbiphenyls, we found that the ICl treatment led to ipso cyclization to give bicyclic spirocyclohexadienones. In the presence of MeOH/H2SO4, these spiroketone products undergo rearrangement to give 9-iodophenanthrenes through a selective 1,2-alkenyl migration. We prepared various 4‘-methoxy-2-ethynylbiphenyl compounds to show the generalization of such an ipso cyclization and 1,2-alkenyl shift. This ipso-cyclization approach can be extended to the preparation of dibenzo[g,p]chrysenes.</description><subject>Chemistry</subject><subject>Condensed benzenic and aromatic compounds</subject><subject>Exact sciences and technology</subject><subject>Noncondensed benzenic compounds</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2007</creationdate><recordtype>article</recordtype><recordid>eNptkMtu1DAUhiMEokNhwQsgb0BUIuBLHDtLCJcZUQR0CkJFyHJsp3XHsQc7QWR27FjziDwJgRl1NpzNWZxPv_7zZdldBB8jiNGTy8AgorDormUzRDHMywoW17MZhBjnBJfkILuV0iWchlJ6MztArGKEYj7LfixH31-YZBMILXhuG-M34fP5o_UXdRHHZLxJoI2hA89sethYGUd3JJXpR_fv9M1KsDRfB-N7Kx1Y1C5feD0oo0E9Kmc3srfBA-k1eGM3IYaV_f3z19yoFajDsHbWn9_ObrTSJXNntw-zDy9fnNbz_Pjtq0X99DiXpMR9TqhuZYFYq3lJy4qVuoGcaAh52yBSICKRVphTWhRaMqQ5b0tcwYaXBVUYEnKYPdjmrmOYCqdedDYp45z0JgxJlJwixhGewKMtqGJIKZpWrKPtps8FguKvb3Hle2Lv7UKHpjN6T-4ET8D9HSCTkq6N0iub9lzFGYO8mrh8y9nUm-9XdxlXomSEUXH6binO3r_-ePLp7ETM97lSpanPEP3k7j8F_wCUXKVm</recordid><startdate>20071123</startdate><enddate>20071123</enddate><creator>Li, Chia-Wen</creator><creator>Wang, Cheng-I</creator><creator>Liao, Hsin-Yi</creator><creator>Chaudhuri, Rupsha</creator><creator>Liu, Rai-Shung</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20071123</creationdate><title>Synthesis of Dibenzo[g,p]chrysenes from Bis(biaryl)acetylenes via Sequential ICl-Induced Cyclization and Mizoroki−Heck Coupling</title><author>Li, Chia-Wen ; Wang, Cheng-I ; Liao, Hsin-Yi ; Chaudhuri, Rupsha ; Liu, Rai-Shung</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a362t-35dfa417fd8656976db083d008fb13413a1dc285544da71d88f6290b8645c2033</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2007</creationdate><topic>Chemistry</topic><topic>Condensed benzenic and aromatic compounds</topic><topic>Exact sciences and technology</topic><topic>Noncondensed benzenic compounds</topic><topic>Organic chemistry</topic><topic>Preparations and properties</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Chia-Wen</creatorcontrib><creatorcontrib>Wang, Cheng-I</creatorcontrib><creatorcontrib>Liao, Hsin-Yi</creatorcontrib><creatorcontrib>Chaudhuri, Rupsha</creatorcontrib><creatorcontrib>Liu, Rai-Shung</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Chia-Wen</au><au>Wang, Cheng-I</au><au>Liao, Hsin-Yi</au><au>Chaudhuri, Rupsha</au><au>Liu, Rai-Shung</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Dibenzo[g,p]chrysenes from Bis(biaryl)acetylenes via Sequential ICl-Induced Cyclization and Mizoroki−Heck Coupling</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2007-11-23</date><risdate>2007</risdate><volume>72</volume><issue>24</issue><spage>9203</spage><epage>9207</epage><pages>9203-9207</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>We report a facile synthesis of functionalized dibenzo[g,p]chrysenes via initial ICl-promoted cyclization of bis(biaryl)acetylenes, followed by the Mizoroki−Heck coupling reaction. This new approach works well for various bis(biaryl)acetylenes to afford dibenzo[g,p]chrysenes bearing various functionalities. With substrates of one special type including 4‘-methoxy-2-ethynylbiphenyls, we found that the ICl treatment led to ipso cyclization to give bicyclic spirocyclohexadienones. In the presence of MeOH/H2SO4, these spiroketone products undergo rearrangement to give 9-iodophenanthrenes through a selective 1,2-alkenyl migration. We prepared various 4‘-methoxy-2-ethynylbiphenyl compounds to show the generalization of such an ipso cyclization and 1,2-alkenyl shift. This ipso-cyclization approach can be extended to the preparation of dibenzo[g,p]chrysenes.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>17973528</pmid><doi>10.1021/jo701504m</doi><tpages>5</tpages></addata></record> |
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| source | American Chemical Society Journals |
| subjects | Chemistry Condensed benzenic and aromatic compounds Exact sciences and technology Noncondensed benzenic compounds Organic chemistry Preparations and properties |
| title | Synthesis of Dibenzo[g,p]chrysenes from Bis(biaryl)acetylenes via Sequential ICl-Induced Cyclization and Mizoroki−Heck Coupling |
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