Brønsted Acid-Catalyzed Cascade Reactions Involving 1,2-Indole Migration
A cascade reaction of indoles with propargylic diols involving an unprecedented metal‐free 1,2‐indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2‐migration a...
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| Veröffentlicht in: | Chemistry : a European journal 2015-09, Vol.21 (37), p.12889-12893 |
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| container_end_page | 12893 |
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| container_issue | 37 |
| container_start_page | 12889 |
| container_title | Chemistry : a European journal |
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| creator | Álvarez, Estela Nieto Faza, Olalla Silva López, Carlos Fernández-Rodríguez, Manuel A. Sanz, Roberto |
| description | A cascade reaction of indoles with propargylic diols involving an unprecedented metal‐free 1,2‐indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2‐migration and subsequent Nazarov cyclization. This Brønsted acid‐catalyzed protocol affords indole‐functionalized benzofulvene derivatives in high yields.
A Brønsted acid‐catalyzed cascade reaction involving an unprecedented metal‐free‐promoted 1,2‐indole migration onto an alkyne has been developed. The reaction of simple indoles with propargylic diols furnishes 2‐indol‐3‐ylbenzofulvenes in high yields and wide scope producing only water as a side product. The proposed mechanism was supported by DFT calculations. |
| doi_str_mv | 10.1002/chem.201502174 |
| format | Article |
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A Brønsted acid‐catalyzed cascade reaction involving an unprecedented metal‐free‐promoted 1,2‐indole migration onto an alkyne has been developed. The reaction of simple indoles with propargylic diols furnishes 2‐indol‐3‐ylbenzofulvenes in high yields and wide scope producing only water as a side product. The proposed mechanism was supported by DFT calculations.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201502174</identifier><identifier>PMID: 26211757</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>benzofulvenes ; Brønsted acid ; catalysis ; Chemistry ; indole migration ; Nazarov cyclization</subject><ispartof>Chemistry : a European journal, 2015-09, Vol.21 (37), p.12889-12893</ispartof><rights>2015 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c5844-7a580b62834742ba12827a1eed3be4f37ca40f16a68c0d2474bfeef9313c4b263</citedby><cites>FETCH-LOGICAL-c5844-7a580b62834742ba12827a1eed3be4f37ca40f16a68c0d2474bfeef9313c4b263</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fchem.201502174$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201502174$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/26211757$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Álvarez, Estela</creatorcontrib><creatorcontrib>Nieto Faza, Olalla</creatorcontrib><creatorcontrib>Silva López, Carlos</creatorcontrib><creatorcontrib>Fernández-Rodríguez, Manuel A.</creatorcontrib><creatorcontrib>Sanz, Roberto</creatorcontrib><title>Brønsted Acid-Catalyzed Cascade Reactions Involving 1,2-Indole Migration</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A cascade reaction of indoles with propargylic diols involving an unprecedented metal‐free 1,2‐indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2‐migration and subsequent Nazarov cyclization. This Brønsted acid‐catalyzed protocol affords indole‐functionalized benzofulvene derivatives in high yields.
A Brønsted acid‐catalyzed cascade reaction involving an unprecedented metal‐free‐promoted 1,2‐indole migration onto an alkyne has been developed. The reaction of simple indoles with propargylic diols furnishes 2‐indol‐3‐ylbenzofulvenes in high yields and wide scope producing only water as a side product. The proposed mechanism was supported by DFT calculations.</description><subject>benzofulvenes</subject><subject>Brønsted acid</subject><subject>catalysis</subject><subject>Chemistry</subject><subject>indole migration</subject><subject>Nazarov cyclization</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2015</creationdate><recordtype>article</recordtype><recordid>eNqFkctKw0AUhgdRtF62LiXgxoWpc59kqUFt8QaiKG6GyeREo2lSZ1q1Ppl7X8wp1SJuXA2H-f6fw3cQ2iS4SzCme_YBBl2KicCUKL6AOkRQEjMlxSLq4JSrWAqWrqBV7x8xxqlkbBmtUEkJUUJ1UP_AfX40fgRFtG-rIs7MyNST9zBmxltTQHQJxo6qtvFRv3lp65equY_ILo37TdHWEJ1V985M_9fRUmlqDxvf7xq6Pjq8ynrx6cVxP9s_ja1IOI-VEQnOJU0YV5zmhtCEKkMACpYDL5myhuOSSCMTiwsaoLwEKFNGmOU5lWwN7cx6h659HoMf6UHlLdS1aaAde00UTojkQiQB3f6DPrZj14TtAiWlShXFIlDdGWVd672DUg9dNTBuognWU8l6KlnPJYfA1nftOB9AMcd_rAYgnQGvVQ2Tf-p01js8-10ez7JVOMrbPGvck5aKKaFvzo81Zb3by7tM6RP2BWiYljc</recordid><startdate>20150907</startdate><enddate>20150907</enddate><creator>Álvarez, Estela</creator><creator>Nieto Faza, Olalla</creator><creator>Silva López, Carlos</creator><creator>Fernández-Rodríguez, Manuel A.</creator><creator>Sanz, Roberto</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope></search><sort><creationdate>20150907</creationdate><title>Brønsted Acid-Catalyzed Cascade Reactions Involving 1,2-Indole Migration</title><author>Álvarez, Estela ; Nieto Faza, Olalla ; Silva López, Carlos ; Fernández-Rodríguez, Manuel A. ; Sanz, Roberto</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c5844-7a580b62834742ba12827a1eed3be4f37ca40f16a68c0d2474bfeef9313c4b263</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2015</creationdate><topic>benzofulvenes</topic><topic>Brønsted acid</topic><topic>catalysis</topic><topic>Chemistry</topic><topic>indole migration</topic><topic>Nazarov cyclization</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Álvarez, Estela</creatorcontrib><creatorcontrib>Nieto Faza, Olalla</creatorcontrib><creatorcontrib>Silva López, Carlos</creatorcontrib><creatorcontrib>Fernández-Rodríguez, Manuel A.</creatorcontrib><creatorcontrib>Sanz, Roberto</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Álvarez, Estela</au><au>Nieto Faza, Olalla</au><au>Silva López, Carlos</au><au>Fernández-Rodríguez, Manuel A.</au><au>Sanz, Roberto</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Brønsted Acid-Catalyzed Cascade Reactions Involving 1,2-Indole Migration</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2015-09-07</date><risdate>2015</risdate><volume>21</volume><issue>37</issue><spage>12889</spage><epage>12893</epage><pages>12889-12893</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>A cascade reaction of indoles with propargylic diols involving an unprecedented metal‐free 1,2‐indole migration onto an alkyne was carried out. DFT calculations support a mechanism consisting of a concerted nucleophilic attack of the indole nucleus with loss of water, followed by the 1,2‐migration and subsequent Nazarov cyclization. This Brønsted acid‐catalyzed protocol affords indole‐functionalized benzofulvene derivatives in high yields.
A Brønsted acid‐catalyzed cascade reaction involving an unprecedented metal‐free‐promoted 1,2‐indole migration onto an alkyne has been developed. The reaction of simple indoles with propargylic diols furnishes 2‐indol‐3‐ylbenzofulvenes in high yields and wide scope producing only water as a side product. The proposed mechanism was supported by DFT calculations.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><pmid>26211757</pmid><doi>10.1002/chem.201502174</doi><tpages>5</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | benzofulvenes Brønsted acid catalysis Chemistry indole migration Nazarov cyclization |
| title | Brønsted Acid-Catalyzed Cascade Reactions Involving 1,2-Indole Migration |
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