Designs and Strategies for the Halo‐Functionalization of Diazo Compounds

Organo halides and their derivatives have received much attention in both the design and development of new synthetic reagents, drugs, and functional materials. In this review, we provide a comprehensive summary of recent advances and strategies in the halo‐functionalization of diazo compounds, incl...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2018-09, Vol.360 (17), p.3185-3212
Main Authors: Khanal, Hari Datta, Thombal, Raju S., Maezono, Shizuka Mei B., Lee, Yong Rok
Format: Article
Language:English
Subjects:
Chemical compounds
diazo compounds
dihaloolefination
Halides
Halogenation
Organic chemistry
Reagents
trifluoromethylation
trifluoromethylthiolation
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
cited_by cdi_FETCH-LOGICAL-c3540-868098972b37499af7ed53485c2f3fac8f0f98ddfc881146e319c0185f15be1c3
cites cdi_FETCH-LOGICAL-c3540-868098972b37499af7ed53485c2f3fac8f0f98ddfc881146e319c0185f15be1c3
container_end_page 3212
container_issue 17
container_start_page 3185
container_title Advanced synthesis & catalysis
container_volume 360
creator Khanal, Hari Datta
Thombal, Raju S.
Maezono, Shizuka Mei B.
Lee, Yong Rok
description Organo halides and their derivatives have received much attention in both the design and development of new synthetic reagents, drugs, and functional materials. In this review, we provide a comprehensive summary of recent advances and strategies in the halo‐functionalization of diazo compounds, including halogenation, dihalogenation, dihaloolefination, trifluoromethylation, trifluoromethylthiolation, and trifluoromethoxylation, using diverse halogenating agents. Special emphasis is placed on the challenges and achievements of these halogenation strategies. For selected examples, mechanisms leading to unusual reactivities and selectivities are discussed in detail to show the impressive and unique properties of these halogenation reactions. Furthermore, we hope to encourage the scientific community to explore the benefits of using diazo compounds as a straightforward and step‐economic alternative approach to the construction of carbon‐halogen bonds.
doi_str_mv 10.1002/adsc.201800340
format article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_journals_2098632023</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2098632023</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3540-868098972b37499af7ed53485c2f3fac8f0f98ddfc881146e319c0185f15be1c3</originalsourceid><addsrcrecordid>eNqFkL1OwzAUhS0EEqWwMltiTrm282OPVUopCImhMFuuYxdXaVzsRKideASekSchVVEZme4Zznd07kHomsCIANBbVUU9okA4AEvhBA1ITrIkJbk4PeoMztFFjCsAUvCiGKDHiYlu2USsmgrP26Bas3QmYusDbt8Mnqnaf39-TbtGt843qnY7tRfYWzxxaudx6dcb3zVVvERnVtXRXP3eIXqd3r2Us-Tp-f6hHD8lmmUpJDznILgo6IIVqRDKFqbKWMozTS2zSnMLVvCqsppzQtLcMCJ0_1VmSbYwRLMhujnkboJ_70xs5cp3oa8WJe2Tc0aBst41Orh08DEGY-UmuLUKW0lA7veS-73kca8eEAfgw9Vm-49bjifz8o_9Af-Jbxw</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2098632023</pqid></control><display><type>article</type><title>Designs and Strategies for the Halo‐Functionalization of Diazo Compounds</title><source>Wiley</source><creator>Khanal, Hari Datta ; Thombal, Raju S. ; Maezono, Shizuka Mei B. ; Lee, Yong Rok</creator><creatorcontrib>Khanal, Hari Datta ; Thombal, Raju S. ; Maezono, Shizuka Mei B. ; Lee, Yong Rok</creatorcontrib><description>Organo halides and their derivatives have received much attention in both the design and development of new synthetic reagents, drugs, and functional materials. In this review, we provide a comprehensive summary of recent advances and strategies in the halo‐functionalization of diazo compounds, including halogenation, dihalogenation, dihaloolefination, trifluoromethylation, trifluoromethylthiolation, and trifluoromethoxylation, using diverse halogenating agents. Special emphasis is placed on the challenges and achievements of these halogenation strategies. For selected examples, mechanisms leading to unusual reactivities and selectivities are discussed in detail to show the impressive and unique properties of these halogenation reactions. Furthermore, we hope to encourage the scientific community to explore the benefits of using diazo compounds as a straightforward and step‐economic alternative approach to the construction of carbon‐halogen bonds.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201800340</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Chemical compounds ; diazo compounds ; dihaloolefination ; Halides ; Halogenation ; Organic chemistry ; Reagents ; trifluoromethylation ; trifluoromethylthiolation</subject><ispartof>Advanced synthesis &amp; catalysis, 2018-09, Vol.360 (17), p.3185-3212</ispartof><rights>2018 Wiley‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3540-868098972b37499af7ed53485c2f3fac8f0f98ddfc881146e319c0185f15be1c3</citedby><cites>FETCH-LOGICAL-c3540-868098972b37499af7ed53485c2f3fac8f0f98ddfc881146e319c0185f15be1c3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Khanal, Hari Datta</creatorcontrib><creatorcontrib>Thombal, Raju S.</creatorcontrib><creatorcontrib>Maezono, Shizuka Mei B.</creatorcontrib><creatorcontrib>Lee, Yong Rok</creatorcontrib><title>Designs and Strategies for the Halo‐Functionalization of Diazo Compounds</title><title>Advanced synthesis &amp; catalysis</title><description>Organo halides and their derivatives have received much attention in both the design and development of new synthetic reagents, drugs, and functional materials. In this review, we provide a comprehensive summary of recent advances and strategies in the halo‐functionalization of diazo compounds, including halogenation, dihalogenation, dihaloolefination, trifluoromethylation, trifluoromethylthiolation, and trifluoromethoxylation, using diverse halogenating agents. Special emphasis is placed on the challenges and achievements of these halogenation strategies. For selected examples, mechanisms leading to unusual reactivities and selectivities are discussed in detail to show the impressive and unique properties of these halogenation reactions. Furthermore, we hope to encourage the scientific community to explore the benefits of using diazo compounds as a straightforward and step‐economic alternative approach to the construction of carbon‐halogen bonds.</description><subject>Chemical compounds</subject><subject>diazo compounds</subject><subject>dihaloolefination</subject><subject>Halides</subject><subject>Halogenation</subject><subject>Organic chemistry</subject><subject>Reagents</subject><subject>trifluoromethylation</subject><subject>trifluoromethylthiolation</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkL1OwzAUhS0EEqWwMltiTrm282OPVUopCImhMFuuYxdXaVzsRKideASekSchVVEZme4Zznd07kHomsCIANBbVUU9okA4AEvhBA1ITrIkJbk4PeoMztFFjCsAUvCiGKDHiYlu2USsmgrP26Bas3QmYusDbt8Mnqnaf39-TbtGt843qnY7tRfYWzxxaudx6dcb3zVVvERnVtXRXP3eIXqd3r2Us-Tp-f6hHD8lmmUpJDznILgo6IIVqRDKFqbKWMozTS2zSnMLVvCqsppzQtLcMCJ0_1VmSbYwRLMhujnkboJ_70xs5cp3oa8WJe2Tc0aBst41Orh08DEGY-UmuLUKW0lA7veS-73kca8eEAfgw9Vm-49bjifz8o_9Af-Jbxw</recordid><startdate>20180903</startdate><enddate>20180903</enddate><creator>Khanal, Hari Datta</creator><creator>Thombal, Raju S.</creator><creator>Maezono, Shizuka Mei B.</creator><creator>Lee, Yong Rok</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20180903</creationdate><title>Designs and Strategies for the Halo‐Functionalization of Diazo Compounds</title><author>Khanal, Hari Datta ; Thombal, Raju S. ; Maezono, Shizuka Mei B. ; Lee, Yong Rok</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3540-868098972b37499af7ed53485c2f3fac8f0f98ddfc881146e319c0185f15be1c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Chemical compounds</topic><topic>diazo compounds</topic><topic>dihaloolefination</topic><topic>Halides</topic><topic>Halogenation</topic><topic>Organic chemistry</topic><topic>Reagents</topic><topic>trifluoromethylation</topic><topic>trifluoromethylthiolation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Khanal, Hari Datta</creatorcontrib><creatorcontrib>Thombal, Raju S.</creatorcontrib><creatorcontrib>Maezono, Shizuka Mei B.</creatorcontrib><creatorcontrib>Lee, Yong Rok</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 &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Khanal, Hari Datta</au><au>Thombal, Raju S.</au><au>Maezono, Shizuka Mei B.</au><au>Lee, Yong Rok</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Designs and Strategies for the Halo‐Functionalization of Diazo Compounds</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><date>2018-09-03</date><risdate>2018</risdate><volume>360</volume><issue>17</issue><spage>3185</spage><epage>3212</epage><pages>3185-3212</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>Organo halides and their derivatives have received much attention in both the design and development of new synthetic reagents, drugs, and functional materials. In this review, we provide a comprehensive summary of recent advances and strategies in the halo‐functionalization of diazo compounds, including halogenation, dihalogenation, dihaloolefination, trifluoromethylation, trifluoromethylthiolation, and trifluoromethoxylation, using diverse halogenating agents. Special emphasis is placed on the challenges and achievements of these halogenation strategies. For selected examples, mechanisms leading to unusual reactivities and selectivities are discussed in detail to show the impressive and unique properties of these halogenation reactions. Furthermore, we hope to encourage the scientific community to explore the benefits of using diazo compounds as a straightforward and step‐economic alternative approach to the construction of carbon‐halogen bonds.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201800340</doi><tpages>28</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2018-09, Vol.360 (17), p.3185-3212
issn 1615-4150
1615-4169
language eng
recordid cdi_proquest_journals_2098632023
source Wiley
subjects Chemical compounds
diazo compounds
dihaloolefination
Halides
Halogenation
Organic chemistry
Reagents
trifluoromethylation
trifluoromethylthiolation
title Designs and Strategies for the Halo‐Functionalization of Diazo Compounds
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-07T15%3A10%3A25IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Designs%20and%20Strategies%20for%20the%20Halo%E2%80%90Functionalization%20of%20Diazo%20Compounds&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Khanal,%20Hari%20Datta&rft.date=2018-09-03&rft.volume=360&rft.issue=17&rft.spage=3185&rft.epage=3212&rft.pages=3185-3212&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201800340&rft_dat=%3Cproquest_cross%3E2098632023%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3540-868098972b37499af7ed53485c2f3fac8f0f98ddfc881146e319c0185f15be1c3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2098632023&rft_id=info:pmid/&rfr_iscdi=true