Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor
We herein describe an alkylation reaction of indoles with NHC salts to access bis(indolyl)methanes as product. The NHC salt (or free NHC) serves as a C1 precursor due to decomposition of its N-heterocyclic ring. Although the exact roles of zinc powder and acetic/formic acid remain elusive, both of t...
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Veröffentlicht in: | Organic & biomolecular chemistry 2024-11, Vol.22 (46), p.958-962 |
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creator | Zhou, Bingwei Gao, Zhao Yang, Yanhao Hu, Yuanyuan |
description | We herein describe an alkylation reaction of indoles with NHC salts to access bis(indolyl)methanes as product. The NHC salt (or free NHC) serves as a C1 precursor due to decomposition of its N-heterocyclic ring. Although the exact roles of zinc powder and acetic/formic acid remain elusive, both of them are indispensable for this reaction. Two possible reaction pathways are proposed based on the results of mechanistic experiments.
We describe an alkylation reaction of indoles with N-heterocyclic carbene (NHC) salts to access bis(indolyl)methanes where the NHC salt serves as a C1 precursor. |
doi_str_mv | 10.1039/d4ob01568a |
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We describe an alkylation reaction of indoles with N-heterocyclic carbene (NHC) salts to access bis(indolyl)methanes where the NHC salt serves as a C1 precursor.</description><subject>Alkylation</subject><subject>Decomposition reactions</subject><subject>Formic acid</subject><subject>Indoles</subject><subject>Precursors</subject><issn>1477-0520</issn><issn>1477-0539</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpd0c9LwzAUB_AgipvTi3cl4GUK1aRJ0-Y4508Y7qA7lzRNXUfbzLz20P_ezM0JksML5MPjvW8QOqfklhIm73JuM0IjkagDNKQ8jgMSMXm4v4dkgE4AVoRQGQt-jAZMciYYpUO0eO-bdmmgBGwLnJUwLpvcVn11XZt2qRoDuIOy-cRvwdK0xlnd66rUWCuXmcZgUFWLFWCFpxSvndGdA-tO0VGhKjBnuzpCi6fHj-lLMJs_v04ns0CHoWgDqriSImeZziLJKTWChLHiudCcMV8TmZOCJlHEORckZ5GJCYmIlgXlGdcJG6Hxtu_a2a_OQJvWJWhTVX5w20HqV5SbI6mnV__oynau8dN5xRiLGYmFVzdbpZ0FcKZI166sletTStJN2OkDn9__hD3x-HLXsstqk-_pb7oeXGyBA71__fst9g1pU4Gn</recordid><startdate>20241127</startdate><enddate>20241127</enddate><creator>Zhou, Bingwei</creator><creator>Gao, Zhao</creator><creator>Yang, Yanhao</creator><creator>Hu, Yuanyuan</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-8014-5482</orcidid></search><sort><creationdate>20241127</creationdate><title>Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor</title><author>Zhou, Bingwei ; Gao, Zhao ; Yang, Yanhao ; Hu, Yuanyuan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c226t-1a4a96d3bcb59411e6027a4d6c433a4d89d0f185544460d35e70050c9f14b4c83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkylation</topic><topic>Decomposition reactions</topic><topic>Formic acid</topic><topic>Indoles</topic><topic>Precursors</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Bingwei</creatorcontrib><creatorcontrib>Gao, Zhao</creatorcontrib><creatorcontrib>Yang, Yanhao</creatorcontrib><creatorcontrib>Hu, Yuanyuan</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhou, Bingwei</au><au>Gao, Zhao</au><au>Yang, Yanhao</au><au>Hu, Yuanyuan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2024-11-27</date><risdate>2024</risdate><volume>22</volume><issue>46</issue><spage>958</spage><epage>962</epage><pages>958-962</pages><issn>1477-0520</issn><issn>1477-0539</issn><eissn>1477-0539</eissn><abstract>We herein describe an alkylation reaction of indoles with NHC salts to access bis(indolyl)methanes as product. The NHC salt (or free NHC) serves as a C1 precursor due to decomposition of its N-heterocyclic ring. Although the exact roles of zinc powder and acetic/formic acid remain elusive, both of them are indispensable for this reaction. Two possible reaction pathways are proposed based on the results of mechanistic experiments.
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subjects | Alkylation Decomposition reactions Formic acid Indoles Precursors |
title | Synthesis of bis(indolyl)methanes using N-heterocyclic carbene salt as a C1 precursor |
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