One‐Step Synthesis of Arylacetaldehydes from Aryl Aldehydes or Diaryl Ketones via One‐Carbon Extension by Using the System of DMSO/KOH/Zinc
A one‐step protocol is described for the synthesis of arylacetaldehydes from aryl aldehydes or diaryl ketones by using the system of DMSO/KOH/zinc. In this transformation, DMSO provides a methine fragment that converts the −CHO structure in aryl aldehydes or the −CO− structure in diaryl ketones to t...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2022-09, Vol.364 (17), p.2989-2995 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Nie, Zhiwen Yang, Tonglin Su, Miaodong Luo, Weiping Liu, Qiang Guo, Cancheng |
| description | A one‐step protocol is described for the synthesis of arylacetaldehydes from aryl aldehydes or diaryl ketones by using the system of DMSO/KOH/zinc. In this transformation, DMSO provides a methine fragment that converts the −CHO structure in aryl aldehydes or the −CO− structure in diaryl ketones to the −CH2CHO structure in arylacetaldehydes via a one‐carbon extension. This protocol could also be used to synthesize arylacetaldehyde acetals from aryl aldehydes or diaryl ketones when zinc was replaced by diols. In this protocol, 25 examples of arylacetaldehydes and 26 examples of arylacetaldehyde acetals have been synthesized from aryl aldehydes or diaryl ketones. Based on control experiments and the literature, a plausible reaction mechanism is proposed in our work. |
| doi_str_mv | 10.1002/adsc.202200437 |
| format | Article |
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In this transformation, DMSO provides a methine fragment that converts the −CHO structure in aryl aldehydes or the −CO− structure in diaryl ketones to the −CH2CHO structure in arylacetaldehydes via a one‐carbon extension. This protocol could also be used to synthesize arylacetaldehyde acetals from aryl aldehydes or diaryl ketones when zinc was replaced by diols. In this protocol, 25 examples of arylacetaldehydes and 26 examples of arylacetaldehyde acetals have been synthesized from aryl aldehydes or diaryl ketones. 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In this transformation, DMSO provides a methine fragment that converts the −CHO structure in aryl aldehydes or the −CO− structure in diaryl ketones to the −CH2CHO structure in arylacetaldehydes via a one‐carbon extension. This protocol could also be used to synthesize arylacetaldehyde acetals from aryl aldehydes or diaryl ketones when zinc was replaced by diols. In this protocol, 25 examples of arylacetaldehydes and 26 examples of arylacetaldehyde acetals have been synthesized from aryl aldehydes or diaryl ketones. Based on control experiments and the literature, a plausible reaction mechanism is proposed in our work.</description><subject>Acetals</subject><subject>Aldehydes</subject><subject>Aromatic compounds</subject><subject>Aryl aldehydes or Diaryl ketones</subject><subject>Arylacetaldehydes</subject><subject>Carbon</subject><subject>Diols</subject><subject>DMSO</subject><subject>Ketones</subject><subject>KOH</subject><subject>One-Carbon Extension</subject><subject>Reaction mechanisms</subject><subject>Synthesis</subject><subject>Zinc</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNqFUMtOg0AUJUYTa3XrehLXtDPDwDBLQqs1rWGB3bghA3OxNBTqDD7Y-Qf6jX6JIKYuXd2Tk_PIPZZ1SfCEYEynUplsQjGlGDOHH1kj4hHXZsQTxwfs4lPrzJgtxoT7nI-sj6iCr_fPuIE9ituq2YApDKpzFOi2lBk0slSwaRUYlOt690Oj4MDVGs0K2XNLaOqqY14KiYbMUOq0rtD8rYHKFB1KW7Q2RfWIupauzDSw65tmd3E0XUaL6UNRZefWSS5LAxe_d2ytr-f34cJeRTe3YbCyM8o4t6VSTKmMcJ56MiMqFVQ4IED4QMFTnDgyw9JlkrsEXFdAiiUjElPGfIKpcsbW1ZC71_XTM5gm2dbPuuoqE8qx8IXPXKdTTQZVpmtjNOTJXhe77t-E4KQfPelHTw6jdwYxGF6LEtp_1Ekwi8M_7zfMEYi3</recordid><startdate>20220906</startdate><enddate>20220906</enddate><creator>Nie, Zhiwen</creator><creator>Yang, Tonglin</creator><creator>Su, Miaodong</creator><creator>Luo, Weiping</creator><creator>Liu, Qiang</creator><creator>Guo, Cancheng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0001-8886-8450</orcidid><orcidid>https://orcid.org/0000-0002-8204-9099</orcidid></search><sort><creationdate>20220906</creationdate><title>One‐Step Synthesis of Arylacetaldehydes from Aryl Aldehydes or Diaryl Ketones via One‐Carbon Extension by Using the System of DMSO/KOH/Zinc</title><author>Nie, Zhiwen ; Yang, Tonglin ; Su, Miaodong ; Luo, Weiping ; Liu, Qiang ; Guo, Cancheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2477-add4ddc177b6ac1db9293e9e98e2e6d713ac0a54a751e559eb0a41a02448102d3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>Acetals</topic><topic>Aldehydes</topic><topic>Aromatic compounds</topic><topic>Aryl aldehydes or Diaryl ketones</topic><topic>Arylacetaldehydes</topic><topic>Carbon</topic><topic>Diols</topic><topic>DMSO</topic><topic>Ketones</topic><topic>KOH</topic><topic>One-Carbon Extension</topic><topic>Reaction mechanisms</topic><topic>Synthesis</topic><topic>Zinc</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Nie, Zhiwen</creatorcontrib><creatorcontrib>Yang, Tonglin</creatorcontrib><creatorcontrib>Su, Miaodong</creatorcontrib><creatorcontrib>Luo, Weiping</creatorcontrib><creatorcontrib>Liu, Qiang</creatorcontrib><creatorcontrib>Guo, Cancheng</creatorcontrib><collection>CrossRef</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>Nie, Zhiwen</au><au>Yang, Tonglin</au><au>Su, Miaodong</au><au>Luo, Weiping</au><au>Liu, Qiang</au><au>Guo, Cancheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐Step Synthesis of Arylacetaldehydes from Aryl Aldehydes or Diaryl Ketones via One‐Carbon Extension by Using the System of DMSO/KOH/Zinc</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2022-09-06</date><risdate>2022</risdate><volume>364</volume><issue>17</issue><spage>2989</spage><epage>2995</epage><pages>2989-2995</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A one‐step protocol is described for the synthesis of arylacetaldehydes from aryl aldehydes or diaryl ketones by using the system of DMSO/KOH/zinc. In this transformation, DMSO provides a methine fragment that converts the −CHO structure in aryl aldehydes or the −CO− structure in diaryl ketones to the −CH2CHO structure in arylacetaldehydes via a one‐carbon extension. This protocol could also be used to synthesize arylacetaldehyde acetals from aryl aldehydes or diaryl ketones when zinc was replaced by diols. In this protocol, 25 examples of arylacetaldehydes and 26 examples of arylacetaldehyde acetals have been synthesized from aryl aldehydes or diaryl ketones. Based on control experiments and the literature, a plausible reaction mechanism is proposed in our work.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202200437</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0001-8886-8450</orcidid><orcidid>https://orcid.org/0000-0002-8204-9099</orcidid></addata></record> |
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| subjects | Acetals Aldehydes Aromatic compounds Aryl aldehydes or Diaryl ketones Arylacetaldehydes Carbon Diols DMSO Ketones KOH One-Carbon Extension Reaction mechanisms Synthesis Zinc |
| title | One‐Step Synthesis of Arylacetaldehydes from Aryl Aldehydes or Diaryl Ketones via One‐Carbon Extension by Using the System of DMSO/KOH/Zinc |
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