Regioselective Hydroiodination of Alkynes by in situ‐Generated HI
An efficient and highly selective hydroiodination of alkynes has been reported. The reaction utilizes in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature. The methodology provided the Markovnikov products exclusively from terminal alkynes, and predominate...
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| Veröffentlicht in: | Asian journal of organic chemistry 2020-01, Vol.9 (1), p.73-76 |
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| container_title | Asian journal of organic chemistry |
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| creator | Li, Jiayan Devi Laishram, Ronibala Chen, Jingchao Xu, Dandan Shi, Guangrui Lv, Haiping Fan, Ruifeng Fan, Baomin |
| description | An efficient and highly selective hydroiodination of alkynes has been reported. The reaction utilizes in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature. The methodology provided the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields. The reaction could be performed on a gram‐scale with good yield.
Works on a gram scale too! An efficient and highly selective hydroiodination of alkynes utilizing in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature has been developed. This methodology tolerates alkyl‐, aryl‐ and heteroaryl substituents on the alkyne moiety affording the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields. |
| doi_str_mv | 10.1002/ajoc.201900677 |
| format | Article |
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Works on a gram scale too! An efficient and highly selective hydroiodination of alkynes utilizing in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature has been developed. This methodology tolerates alkyl‐, aryl‐ and heteroaryl substituents on the alkyne moiety affording the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.201900677</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Alkynes ; Ambient temperature ; Hydroiodination ; Iodine ; Isomers ; Molecular hydrogen ; Molecular iodine ; Organic chemistry ; Vinyl iodides</subject><ispartof>Asian journal of organic chemistry, 2020-01, Vol.9 (1), p.73-76</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2020 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3837-d79f5cf34dae363f12caeeec43159cea7ea7d5ed562f7361655e7fe571d836863</citedby><cites>FETCH-LOGICAL-c3837-d79f5cf34dae363f12caeeec43159cea7ea7d5ed562f7361655e7fe571d836863</cites><orcidid>0000-0003-1789-3741</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%2Fajoc.201900677$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.201900677$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1417,27924,27925,45574,45575</link.rule.ids></links><search><creatorcontrib>Li, Jiayan</creatorcontrib><creatorcontrib>Devi Laishram, Ronibala</creatorcontrib><creatorcontrib>Chen, Jingchao</creatorcontrib><creatorcontrib>Xu, Dandan</creatorcontrib><creatorcontrib>Shi, Guangrui</creatorcontrib><creatorcontrib>Lv, Haiping</creatorcontrib><creatorcontrib>Fan, Ruifeng</creatorcontrib><creatorcontrib>Fan, Baomin</creatorcontrib><title>Regioselective Hydroiodination of Alkynes by in situ‐Generated HI</title><title>Asian journal of organic chemistry</title><description>An efficient and highly selective hydroiodination of alkynes has been reported. The reaction utilizes in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature. The methodology provided the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields. The reaction could be performed on a gram‐scale with good yield.
Works on a gram scale too! An efficient and highly selective hydroiodination of alkynes utilizing in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature has been developed. This methodology tolerates alkyl‐, aryl‐ and heteroaryl substituents on the alkyne moiety affording the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields.</description><subject>Alkynes</subject><subject>Ambient temperature</subject><subject>Hydroiodination</subject><subject>Iodine</subject><subject>Isomers</subject><subject>Molecular hydrogen</subject><subject>Molecular iodine</subject><subject>Organic chemistry</subject><subject>Vinyl iodides</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkE1LAzEQhoMoWGqvnhc8b83HJtk9llLbSqEgeg4xmUhq3dRkq-ytF-_-xv4St1Tq0WFg5vC8M_AgdE3wkGBMb_UqmCHFpMJYSHmGepRULOcl4eenHctLNEhphbuSsiK06qHJA7z4kGANpvEfkM1aG4MP1te68aHOgstG69e2hpQ9t5mv97uv5Jvtfvc9hRqibsBms_kVunB6nWDwO_vo6W7yOJ7li-V0Ph4tcsNKJnMrK8eNY4XVwARzhBoNAKZghFcGtOzacrBcUCeZIIJzkA64JLZkohSsj26OdzcxvG8hNWoVtrHuXirKCkJFISXtqOGRMjGkFMGpTfRvOraKYHWwpQ621MlWF6iOgU-_hvYfWo3ul-O_7A9aRXAJ</recordid><startdate>202001</startdate><enddate>202001</enddate><creator>Li, Jiayan</creator><creator>Devi Laishram, Ronibala</creator><creator>Chen, Jingchao</creator><creator>Xu, Dandan</creator><creator>Shi, Guangrui</creator><creator>Lv, Haiping</creator><creator>Fan, Ruifeng</creator><creator>Fan, Baomin</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-1789-3741</orcidid></search><sort><creationdate>202001</creationdate><title>Regioselective Hydroiodination of Alkynes by in situ‐Generated HI</title><author>Li, Jiayan ; Devi Laishram, Ronibala ; Chen, Jingchao ; Xu, Dandan ; Shi, Guangrui ; Lv, Haiping ; Fan, Ruifeng ; Fan, Baomin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3837-d79f5cf34dae363f12caeeec43159cea7ea7d5ed562f7361655e7fe571d836863</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Alkynes</topic><topic>Ambient temperature</topic><topic>Hydroiodination</topic><topic>Iodine</topic><topic>Isomers</topic><topic>Molecular hydrogen</topic><topic>Molecular iodine</topic><topic>Organic chemistry</topic><topic>Vinyl iodides</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Jiayan</creatorcontrib><creatorcontrib>Devi Laishram, Ronibala</creatorcontrib><creatorcontrib>Chen, Jingchao</creatorcontrib><creatorcontrib>Xu, Dandan</creatorcontrib><creatorcontrib>Shi, Guangrui</creatorcontrib><creatorcontrib>Lv, Haiping</creatorcontrib><creatorcontrib>Fan, Ruifeng</creatorcontrib><creatorcontrib>Fan, Baomin</creatorcontrib><collection>CrossRef</collection><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Jiayan</au><au>Devi Laishram, Ronibala</au><au>Chen, Jingchao</au><au>Xu, Dandan</au><au>Shi, Guangrui</au><au>Lv, Haiping</au><au>Fan, Ruifeng</au><au>Fan, Baomin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective Hydroiodination of Alkynes by in situ‐Generated HI</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2020-01</date><risdate>2020</risdate><volume>9</volume><issue>1</issue><spage>73</spage><epage>76</epage><pages>73-76</pages><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>An efficient and highly selective hydroiodination of alkynes has been reported. The reaction utilizes in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature. The methodology provided the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields. The reaction could be performed on a gram‐scale with good yield.
Works on a gram scale too! An efficient and highly selective hydroiodination of alkynes utilizing in situ‐generated HI from [Rh]‐complex, molecular hydrogen, and iodine under ambient temperature has been developed. This methodology tolerates alkyl‐, aryl‐ and heteroaryl substituents on the alkyne moiety affording the Markovnikov products exclusively from terminal alkynes, and predominately E‐isomers from the internal alkynes in good yields.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.201900677</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0003-1789-3741</orcidid></addata></record> |
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| source | Wiley-Blackwell Journals |
| subjects | Alkynes Ambient temperature Hydroiodination Iodine Isomers Molecular hydrogen Molecular iodine Organic chemistry Vinyl iodides |
| title | Regioselective Hydroiodination of Alkynes by in situ‐Generated HI |
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