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One-pot tandem reduction and site-selective halogenation of nitroarenes
Halogenated aryl amines are a widely used chemical feedstock in the pharmaceutical and agrochemical industries. Achieving a single regioselective product from the para -selective halogenation of the aryl ring is significantly challenging because of the presence of several C-H bonds with similar reac...
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| Published in: | Organic & biomolecular chemistry 2024-01, Vol.22 (5), p.976-981 |
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| Main Authors: | , , , , |
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| container_end_page | 981 |
| container_issue | 5 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Dhandabani, Ganesh Kumar Chang, Li-Te Hsieh, Hao-Yu Shih, Chia-Ling Hsin, Ling-Wei |
| description | Halogenated aryl amines are a widely used chemical feedstock in the pharmaceutical and agrochemical industries. Achieving a single regioselective product from the
para
-selective halogenation of the aryl ring is significantly challenging because of the presence of several C-H bonds with similar reactivities. In this study, single
para
-halogenated aniline derivatives were prepared by the cascade
para
-selective halogenation (Cl, Br) and reduction of nitrobenzene derivatives using a mixture of SnCl
2
/SnCl
4
salts. The mechanistic study confirmed that the noncovalent interactions between the chalcogen bond and Sn salt were pivotal for achieving regioselectivity. This synthetic method was applied for the development of potent and highly selective positron emission tomography molecular probes for serotonin transporters.
Halogenated aryl amines are a widely used chemical feedstock in the pharmaceutical and agrochemical industries. |
| doi_str_mv | 10.1039/d3ob01732j |
| format | article |
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para
-selective halogenation of the aryl ring is significantly challenging because of the presence of several C-H bonds with similar reactivities. In this study, single
para
-halogenated aniline derivatives were prepared by the cascade
para
-selective halogenation (Cl, Br) and reduction of nitrobenzene derivatives using a mixture of SnCl
2
/SnCl
4
salts. The mechanistic study confirmed that the noncovalent interactions between the chalcogen bond and Sn salt were pivotal for achieving regioselectivity. This synthetic method was applied for the development of potent and highly selective positron emission tomography molecular probes for serotonin transporters.
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para
-selective halogenation of the aryl ring is significantly challenging because of the presence of several C-H bonds with similar reactivities. In this study, single
para
-halogenated aniline derivatives were prepared by the cascade
para
-selective halogenation (Cl, Br) and reduction of nitrobenzene derivatives using a mixture of SnCl
2
/SnCl
4
salts. The mechanistic study confirmed that the noncovalent interactions between the chalcogen bond and Sn salt were pivotal for achieving regioselectivity. This synthetic method was applied for the development of potent and highly selective positron emission tomography molecular probes for serotonin transporters.
Halogenated aryl amines are a widely used chemical feedstock in the pharmaceutical and agrochemical industries.</description><subject>Agrochemicals</subject><subject>Amines</subject><subject>Aniline</subject><subject>Aromatic compounds</subject><subject>Chalcogen bonds</subject><subject>Halogenation</subject><subject>Nitrobenzene</subject><subject>Positron emission</subject><subject>Positron emission tomography</subject><subject>Reduction</subject><subject>Regioselectivity</subject><subject>Serotonin</subject><subject>Serotonin transporter</subject><subject>Stannic chloride</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpd0c9LwzAUB_AgitPpxbtS8CJCNWna_Djq1KkMdtFzSZMX7WiTmbSC_711mxM8hPx4Hx6PbxA6IfiKYCqvDfUVJpxmix10QHLOU1xQubs9Z3iEDmNcYEwkZ_k-GlFBBMaFPEDTuYN06bukU85AmwQwve5q75LhnsS6gzRCA8PTJyTvqvFv4NSq7m3i6i54FcBBPEJ7VjURjjf7GL0-3L9MHtPZfPo0uZmlOpOsS60oMDNALMEs16pQWlTCMpFLa3LNOGEsJ9YW3BRgpFaVFcNihFCLs8pUdIwu1n2XwX_0ELuyraOGplEOfB_LTGa44JgLMtDzf3Th--CG6VYK51ywbFCXa6WDjzGALZehblX4Kgkuf-It7-j8dhXv84DPNi37qgWzpb95DuB0DULU2-rf_9BvjS1_Hw</recordid><startdate>20240131</startdate><enddate>20240131</enddate><creator>Dhandabani, Ganesh Kumar</creator><creator>Chang, Li-Te</creator><creator>Hsieh, Hao-Yu</creator><creator>Shih, Chia-Ling</creator><creator>Hsin, Ling-Wei</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/0000-0001-5018-4491</orcidid><orcidid>https://orcid.org/0000-0002-4555-8994</orcidid></search><sort><creationdate>20240131</creationdate><title>One-pot tandem reduction and site-selective halogenation of nitroarenes</title><author>Dhandabani, Ganesh Kumar ; Chang, Li-Te ; Hsieh, Hao-Yu ; Shih, Chia-Ling ; Hsin, Ling-Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c296t-f8506de1f1064ca5ac8b8f6849fd4c6716641ff57d5ed9cabf8abf6113f02bdb3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Agrochemicals</topic><topic>Amines</topic><topic>Aniline</topic><topic>Aromatic compounds</topic><topic>Chalcogen bonds</topic><topic>Halogenation</topic><topic>Nitrobenzene</topic><topic>Positron emission</topic><topic>Positron emission tomography</topic><topic>Reduction</topic><topic>Regioselectivity</topic><topic>Serotonin</topic><topic>Serotonin transporter</topic><topic>Stannic chloride</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Dhandabani, Ganesh Kumar</creatorcontrib><creatorcontrib>Chang, Li-Te</creatorcontrib><creatorcontrib>Hsieh, Hao-Yu</creatorcontrib><creatorcontrib>Shih, Chia-Ling</creatorcontrib><creatorcontrib>Hsin, Ling-Wei</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>Dhandabani, Ganesh Kumar</au><au>Chang, Li-Te</au><au>Hsieh, Hao-Yu</au><au>Shih, Chia-Ling</au><au>Hsin, Ling-Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One-pot tandem reduction and site-selective halogenation of nitroarenes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2024-01-31</date><risdate>2024</risdate><volume>22</volume><issue>5</issue><spage>976</spage><epage>981</epage><pages>976-981</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Halogenated aryl amines are a widely used chemical feedstock in the pharmaceutical and agrochemical industries. Achieving a single regioselective product from the
para
-selective halogenation of the aryl ring is significantly challenging because of the presence of several C-H bonds with similar reactivities. In this study, single
para
-halogenated aniline derivatives were prepared by the cascade
para
-selective halogenation (Cl, Br) and reduction of nitrobenzene derivatives using a mixture of SnCl
2
/SnCl
4
salts. The mechanistic study confirmed that the noncovalent interactions between the chalcogen bond and Sn salt were pivotal for achieving regioselectivity. This synthetic method was applied for the development of potent and highly selective positron emission tomography molecular probes for serotonin transporters.
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| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2024-01, Vol.22 (5), p.976-981 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_proquest_journals_2920047862 |
| source | Royal Society of Chemistry Journals |
| subjects | Agrochemicals Amines Aniline Aromatic compounds Chalcogen bonds Halogenation Nitrobenzene Positron emission Positron emission tomography Reduction Regioselectivity Serotonin Serotonin transporter Stannic chloride |
| title | One-pot tandem reduction and site-selective halogenation of nitroarenes |
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