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Electrosynthesis of C−3 Phosphorylated 2H-Indazoles from Trialkyl Phosphites and 2H-Indazoles
A facile and efficient direct electrochemical oxidation method for C−3 phosphorylation of 2 H -indazoles with trialkyl phosphites as the phosphorylation reagents has been developed. Introducing electricity to the green and sustainable synthetic procedures allowed the reactions to be carried out unde...
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| Published in: | Journal of the Electrochemical Society 2022-12, Vol.169 (12), p.125501 |
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| Main Authors: | , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c314t-595681d0836c8aa86dc7d35fab08a64fde1a52e8e8c9f1f0e522be8aa2ce74943 |
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| cites | cdi_FETCH-LOGICAL-c314t-595681d0836c8aa86dc7d35fab08a64fde1a52e8e8c9f1f0e522be8aa2ce74943 |
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| container_issue | 12 |
| container_start_page | 125501 |
| container_title | Journal of the Electrochemical Society |
| container_volume | 169 |
| creator | Liu, Xin Yin, Xin Wu, Wenliang She, Yuanbin Zhao, Qian Zhang, Chuanye Li, Meichao Shen, Zhenlu |
| description | A facile and efficient direct electrochemical oxidation method for C−3 phosphorylation of 2
H
-indazoles with trialkyl phosphites as the phosphorylation reagents has been developed. Introducing electricity to the green and sustainable synthetic procedures allowed the reactions to be carried out under simple and mild conditions without any metal salts and additional oxidants. Electrochemical data asserted that the cation radical species which were generated from the oxidation of 2
H
-indazoles were stabilized by 1,1,1,3,3,3-hexafluoro-2-propanol and could be captured by trialkyl phosphites effectively to form C−3 phosphorylated 2
H
-indazoles. In an undivided cell, a board range of functional groups on various substrates were well tolerated and the yield of the desired phosphorylated products was up to 84%. Moreover, a plausible mechanistic proposal involving radical pathway was established based on the results of cyclic voltammetry, in situ FTIR and control experiments. |
| doi_str_mv | 10.1149/1945-7111/acaa04 |
| format | article |
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H
-indazoles with trialkyl phosphites as the phosphorylation reagents has been developed. Introducing electricity to the green and sustainable synthetic procedures allowed the reactions to be carried out under simple and mild conditions without any metal salts and additional oxidants. Electrochemical data asserted that the cation radical species which were generated from the oxidation of 2
H
-indazoles were stabilized by 1,1,1,3,3,3-hexafluoro-2-propanol and could be captured by trialkyl phosphites effectively to form C−3 phosphorylated 2
H
-indazoles. In an undivided cell, a board range of functional groups on various substrates were well tolerated and the yield of the desired phosphorylated products was up to 84%. Moreover, a plausible mechanistic proposal involving radical pathway was established based on the results of cyclic voltammetry, in situ FTIR and control experiments.</description><identifier>ISSN: 0013-4651</identifier><identifier>EISSN: 1945-7111</identifier><identifier>DOI: 10.1149/1945-7111/acaa04</identifier><identifier>CODEN: JESOAN</identifier><language>eng</language><publisher>IOP Publishing</publisher><ispartof>Journal of the Electrochemical Society, 2022-12, Vol.169 (12), p.125501</ispartof><rights>2022 The Electrochemical Society (“ECS”). Published on behalf of ECS by IOP Publishing Limited</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c314t-595681d0836c8aa86dc7d35fab08a64fde1a52e8e8c9f1f0e522be8aa2ce74943</citedby><cites>FETCH-LOGICAL-c314t-595681d0836c8aa86dc7d35fab08a64fde1a52e8e8c9f1f0e522be8aa2ce74943</cites><orcidid>0000-0001-8808-2554 ; 0000-0002-3699-1198</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,777,781,27905,27906</link.rule.ids></links><search><creatorcontrib>Liu, Xin</creatorcontrib><creatorcontrib>Yin, Xin</creatorcontrib><creatorcontrib>Wu, Wenliang</creatorcontrib><creatorcontrib>She, Yuanbin</creatorcontrib><creatorcontrib>Zhao, Qian</creatorcontrib><creatorcontrib>Zhang, Chuanye</creatorcontrib><creatorcontrib>Li, Meichao</creatorcontrib><creatorcontrib>Shen, Zhenlu</creatorcontrib><title>Electrosynthesis of C−3 Phosphorylated 2H-Indazoles from Trialkyl Phosphites and 2H-Indazoles</title><title>Journal of the Electrochemical Society</title><addtitle>JES</addtitle><addtitle>J. Electrochem. Soc</addtitle><description>A facile and efficient direct electrochemical oxidation method for C−3 phosphorylation of 2
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H
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H
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H
-indazoles with trialkyl phosphites as the phosphorylation reagents has been developed. Introducing electricity to the green and sustainable synthetic procedures allowed the reactions to be carried out under simple and mild conditions without any metal salts and additional oxidants. Electrochemical data asserted that the cation radical species which were generated from the oxidation of 2
H
-indazoles were stabilized by 1,1,1,3,3,3-hexafluoro-2-propanol and could be captured by trialkyl phosphites effectively to form C−3 phosphorylated 2
H
-indazoles. In an undivided cell, a board range of functional groups on various substrates were well tolerated and the yield of the desired phosphorylated products was up to 84%. Moreover, a plausible mechanistic proposal involving radical pathway was established based on the results of cyclic voltammetry, in situ FTIR and control experiments.</abstract><pub>IOP Publishing</pub><doi>10.1149/1945-7111/acaa04</doi><tpages>11</tpages><orcidid>https://orcid.org/0000-0001-8808-2554</orcidid><orcidid>https://orcid.org/0000-0002-3699-1198</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0013-4651 |
| ispartof | Journal of the Electrochemical Society, 2022-12, Vol.169 (12), p.125501 |
| issn | 0013-4651 1945-7111 |
| language | eng |
| recordid | cdi_iop_journals_10_1149_1945_7111_acaa04 |
| source | Institute of Physics |
| title | Electrosynthesis of C−3 Phosphorylated 2H-Indazoles from Trialkyl Phosphites and 2H-Indazoles |
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