Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents
The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2‐ketoacetanilides general...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2021-07, Vol.363 (13), p.3245-3249 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Llopis, Natalia Gisbert, Patricia Baeza, Alejandro |
| description | The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. Among these solvents, 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2‐ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans derivatives. Furthermore, the procedure was implemented in a larger‐scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability. |
| doi_str_mv | 10.1002/adsc.202100214 |
| format | Article |
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Among these solvents, 1,1,1,3,3,3‐hexafluoroisopropanol (HFIP) stands out as the one affording the corresponding 2‐ketoacetanilides generally in higher yields The protocol described has also enabled the oxidation of different pyrroles and furans derivatives. Furthermore, the procedure was implemented in a larger‐scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202100214</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Cleavage ; Furans ; HFIP ; Hydrogen Peroxide ; Indoles ; Oxidation ; Pyrroles ; Solvents ; Ureas ; Witkop oxidation</subject><ispartof>Advanced synthesis & catalysis, 2021-07, Vol.363 (13), p.3245-3249</ispartof><rights>2021 The Authors. 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Furthermore, the procedure was implemented in a larger‐scale and HFIP was distilled from the reaction mixture and reused (up to 4 cycles) without a significant detriment in the reaction outcome, which remarks its sustainability and applicability.</description><subject>Cleavage</subject><subject>Furans</subject><subject>HFIP</subject><subject>Hydrogen Peroxide</subject><subject>Indoles</subject><subject>Oxidation</subject><subject>Pyrroles</subject><subject>Solvents</subject><subject>Ureas</subject><subject>Witkop oxidation</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>24P</sourceid><sourceid>WIN</sourceid><recordid>eNo9kM1Lw0AQxRdRsFavnhc8p-73JscSP1qoVKi9eFmm2U1Jidm6m0bz35tS6WneG34zDx5C95RMKCHsEWwsJoywo6HiAo2oojIRVGWXZy3JNbqJcUcI1anWI_S5_K0stFXncF476GDrsC_xvLG-dhG_OVtB6yze9HgdHOBZb4Pfuga_u-CH04EOeMaWDFfDztcQ8MrXnWvaeIuuSqiju_ufY7R-ef7IZ8li-TrPp4tkx3kmEp1JYiVAqhXdKABdUMJcQYFpIlQqgAhdCAvWCkgVLaVUlJfaDpoybjd8jB5Of_fBfx9cbM3OH0IzRBomhSYp4TodqOxE_VS1680-VF8QekOJOfZljuWZc3lm-rTKz47_AeFZY5Y</recordid><startdate>20210701</startdate><enddate>20210701</enddate><creator>Llopis, Natalia</creator><creator>Gisbert, Patricia</creator><creator>Baeza, Alejandro</creator><general>Wiley Subscription Services, Inc</general><scope>24P</scope><scope>WIN</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0002-6230-1162</orcidid></search><sort><creationdate>20210701</creationdate><title>Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents</title><author>Llopis, Natalia ; Gisbert, Patricia ; Baeza, Alejandro</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j3394-7950d5aa8761b6aa7c102ec1a2704684a047c4dadd4a861f55613f7d861123db3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Cleavage</topic><topic>Furans</topic><topic>HFIP</topic><topic>Hydrogen Peroxide</topic><topic>Indoles</topic><topic>Oxidation</topic><topic>Pyrroles</topic><topic>Solvents</topic><topic>Ureas</topic><topic>Witkop oxidation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Llopis, Natalia</creatorcontrib><creatorcontrib>Gisbert, Patricia</creatorcontrib><creatorcontrib>Baeza, Alejandro</creatorcontrib><collection>Wiley Online Library Open Access</collection><collection>Wiley Free Content</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Llopis, Natalia</au><au>Gisbert, Patricia</au><au>Baeza, Alejandro</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2021-07-01</date><risdate>2021</risdate><volume>363</volume><issue>13</issue><spage>3245</spage><epage>3249</epage><pages>3245-3249</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The oxidative cleavage of indoles (Witkop oxidation) involving the use of H2O2 or urea hydrogen peroxide in combination with a polar solvent has been described. 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| subjects | Cleavage Furans HFIP Hydrogen Peroxide Indoles Oxidation Pyrroles Solvents Ureas Witkop oxidation |
| title | Oxidative Cleavage of Indoles Mediated by Urea Hydrogen Peroxide or H2O2 in Polar Solvents |
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