Atom-economical group-transfer reactions with hypervalent iodine compounds

Hypervalent iodine compounds, in particular aryl-λ -iodanes, have been used extensively as electrophilic group-transfer reagents. Even though these compounds are superior substrates in terms of reactivity and stability, their utilization is accompanied by stoichiometric amounts of an aryl iodide as...

Full description

Saved in:
Bibliographic Details
Published in:Beilstein journal of organic chemistry 2018, Vol.14 (1), p.1263-1280
Main Authors: Boelke, Andreas, Finkbeiner, Peter, Nachtsheim, Boris J
Format: Article
Language:English
Subjects:
atom economy
benziodoxolones
Chemical reactions
Chemistry
homogeneous catalysis
hypervalent iodine
Iodine
Iodine compounds
iodonium salts
Ligands
Review
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-c475t-6e0f7755b493054495d458c35e90fbb6d8c81b5776fd987c0da462cd389f0dbe3
cites cdi_FETCH-LOGICAL-c475t-6e0f7755b493054495d458c35e90fbb6d8c81b5776fd987c0da462cd389f0dbe3
container_end_page 1280
container_issue 1
container_start_page 1263
container_title Beilstein journal of organic chemistry
container_volume 14
creator Boelke, Andreas
Finkbeiner, Peter
Nachtsheim, Boris J
description Hypervalent iodine compounds, in particular aryl-λ -iodanes, have been used extensively as electrophilic group-transfer reagents. Even though these compounds are superior substrates in terms of reactivity and stability, their utilization is accompanied by stoichiometric amounts of an aryl iodide as waste. This highly nonpolar side product can be tedious to separate from the desired target molecules and significantly reduces the overall atom efficiency of these transformations. In this short review, we want to give a brief summary of recently developed methods, in which this arising former waste is used as an additional reagent in cascade transformations to generate multiple substituted products in one step and with high atom efficiency.
doi_str_mv 10.3762/bjoc.14.108
format article
fullrecord <record><control><sourceid>proquest_doaj_</sourceid><recordid>TN_cdi_doaj_primary_oai_doaj_org_article_cc0c60adaabc4e71a20a91d47185935e</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><doaj_id>oai_doaj_org_article_cc0c60adaabc4e71a20a91d47185935e</doaj_id><sourcerecordid>2080459236</sourcerecordid><originalsourceid>FETCH-LOGICAL-c475t-6e0f7755b493054495d458c35e90fbb6d8c81b5776fd987c0da462cd389f0dbe3</originalsourceid><addsrcrecordid>eNpdkctrFTEUh4MotlZX7mXAjSBzezJ5b4RSfLQUutF1yCSZe3OZScZkptL_3tRbS9tVXh9fzjk_hN5j2BDBu9N-n-wG0w0G-QIdY8mhZUSJl4_2R-hNKXsAChz4a3TUKSUEUfQYXZ4taWq9TTFNwZqx2ea0zu2STSyDz032xi4hxdL8Ccuu2d3OPt-Y0celCcmF6Bubpjmt0ZW36NVgxuLf3a8n6Ne3rz_Pf7RX198vzs-uWksFW1ruYRCCsZ4qAoxSxRxl0hLmFQx9z520EvdMCD44JYUFZyjvrCNSDeB6T07QxcHrktnrOYfJ5FudTND_LlLeapOXYEevrQXLwThjeku9wKYDo7CjAkum6o_V9eXgmtd-8s7WvrIZn0ifvsSw09t0ozmAwp2qgk_3gpx-r74segrF-nE00ae16A44p0IKTir68Rm6T2uOdVSVkkCZ6giv1OcDZXMqJfvhoRgM-i5vfZe3xrSeZaU_PK7_gf0fMPkL1Byn1g</addsrcrecordid><sourcetype>Open Website</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2080459236</pqid></control><display><type>article</type><title>Atom-economical group-transfer reactions with hypervalent iodine compounds</title><source>Open Access: PubMed Central</source><source>ProQuest - Publicly Available Content Database</source><creator>Boelke, Andreas ; Finkbeiner, Peter ; Nachtsheim, Boris J</creator><creatorcontrib>Boelke, Andreas ; Finkbeiner, Peter ; Nachtsheim, Boris J</creatorcontrib><description>Hypervalent iodine compounds, in particular aryl-λ -iodanes, have been used extensively as electrophilic group-transfer reagents. Even though these compounds are superior substrates in terms of reactivity and stability, their utilization is accompanied by stoichiometric amounts of an aryl iodide as waste. This highly nonpolar side product can be tedious to separate from the desired target molecules and significantly reduces the overall atom efficiency of these transformations. In this short review, we want to give a brief summary of recently developed methods, in which this arising former waste is used as an additional reagent in cascade transformations to generate multiple substituted products in one step and with high atom efficiency.</description><identifier>ISSN: 1860-5397</identifier><identifier>ISSN: 2195-951X</identifier><identifier>EISSN: 1860-5397</identifier><identifier>DOI: 10.3762/bjoc.14.108</identifier><identifier>PMID: 29977394</identifier><language>eng</language><publisher>Germany: Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</publisher><subject>atom economy ; benziodoxolones ; Chemical reactions ; Chemistry ; homogeneous catalysis ; hypervalent iodine ; Iodine ; Iodine compounds ; iodonium salts ; Ligands ; Review</subject><ispartof>Beilstein journal of organic chemistry, 2018, Vol.14 (1), p.1263-1280</ispartof><rights>Copyright © 2018, Boelke et al.; licensee Beilstein-Institut. This work is published under http://creativecommons.org/licenses/by/4.0 (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>Copyright © 2018, Boelke et al. 2018 Boelke et al.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c475t-6e0f7755b493054495d458c35e90fbb6d8c81b5776fd987c0da462cd389f0dbe3</citedby><cites>FETCH-LOGICAL-c475t-6e0f7755b493054495d458c35e90fbb6d8c81b5776fd987c0da462cd389f0dbe3</cites><orcidid>0000-0002-3759-2770</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2080459236/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2080459236?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,4022,25752,27922,27923,27924,37011,37012,44589,53790,53792,74897</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29977394$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Boelke, Andreas</creatorcontrib><creatorcontrib>Finkbeiner, Peter</creatorcontrib><creatorcontrib>Nachtsheim, Boris J</creatorcontrib><title>Atom-economical group-transfer reactions with hypervalent iodine compounds</title><title>Beilstein journal of organic chemistry</title><addtitle>Beilstein J Org Chem</addtitle><description>Hypervalent iodine compounds, in particular aryl-λ -iodanes, have been used extensively as electrophilic group-transfer reagents. Even though these compounds are superior substrates in terms of reactivity and stability, their utilization is accompanied by stoichiometric amounts of an aryl iodide as waste. This highly nonpolar side product can be tedious to separate from the desired target molecules and significantly reduces the overall atom efficiency of these transformations. In this short review, we want to give a brief summary of recently developed methods, in which this arising former waste is used as an additional reagent in cascade transformations to generate multiple substituted products in one step and with high atom efficiency.</description><subject>atom economy</subject><subject>benziodoxolones</subject><subject>Chemical reactions</subject><subject>Chemistry</subject><subject>homogeneous catalysis</subject><subject>hypervalent iodine</subject><subject>Iodine</subject><subject>Iodine compounds</subject><subject>iodonium salts</subject><subject>Ligands</subject><subject>Review</subject><issn>1860-5397</issn><issn>2195-951X</issn><issn>1860-5397</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><sourceid>PIMPY</sourceid><sourceid>DOA</sourceid><recordid>eNpdkctrFTEUh4MotlZX7mXAjSBzezJ5b4RSfLQUutF1yCSZe3OZScZkptL_3tRbS9tVXh9fzjk_hN5j2BDBu9N-n-wG0w0G-QIdY8mhZUSJl4_2R-hNKXsAChz4a3TUKSUEUfQYXZ4taWq9TTFNwZqx2ea0zu2STSyDz032xi4hxdL8Ccuu2d3OPt-Y0celCcmF6Bubpjmt0ZW36NVgxuLf3a8n6Ne3rz_Pf7RX198vzs-uWksFW1ruYRCCsZ4qAoxSxRxl0hLmFQx9z520EvdMCD44JYUFZyjvrCNSDeB6T07QxcHrktnrOYfJ5FudTND_LlLeapOXYEevrQXLwThjeku9wKYDo7CjAkum6o_V9eXgmtd-8s7WvrIZn0ifvsSw09t0ozmAwp2qgk_3gpx-r74segrF-nE00ae16A44p0IKTir68Rm6T2uOdVSVkkCZ6giv1OcDZXMqJfvhoRgM-i5vfZe3xrSeZaU_PK7_gf0fMPkL1Byn1g</recordid><startdate>2018</startdate><enddate>2018</enddate><creator>Boelke, Andreas</creator><creator>Finkbeiner, Peter</creator><creator>Nachtsheim, Boris J</creator><general>Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</general><general>Beilstein-Institut</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7XB</scope><scope>88I</scope><scope>8FE</scope><scope>8FH</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BBNVY</scope><scope>BENPR</scope><scope>BFMQW</scope><scope>BHPHI</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>GNUQQ</scope><scope>HCIFZ</scope><scope>LK8</scope><scope>M2P</scope><scope>M7P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>Q9U</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-3759-2770</orcidid></search><sort><creationdate>2018</creationdate><title>Atom-economical group-transfer reactions with hypervalent iodine compounds</title><author>Boelke, Andreas ; Finkbeiner, Peter ; Nachtsheim, Boris J</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c475t-6e0f7755b493054495d458c35e90fbb6d8c81b5776fd987c0da462cd389f0dbe3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>atom economy</topic><topic>benziodoxolones</topic><topic>Chemical reactions</topic><topic>Chemistry</topic><topic>homogeneous catalysis</topic><topic>hypervalent iodine</topic><topic>Iodine</topic><topic>Iodine compounds</topic><topic>iodonium salts</topic><topic>Ligands</topic><topic>Review</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Boelke, Andreas</creatorcontrib><creatorcontrib>Finkbeiner, Peter</creatorcontrib><creatorcontrib>Nachtsheim, Boris J</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Science Database (Alumni Edition)</collection><collection>ProQuest SciTech Collection</collection><collection>ProQuest Natural Science Collection</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central</collection><collection>ProQuest Central Essentials</collection><collection>Biological Science Collection</collection><collection>AUTh Library subscriptions: ProQuest Central</collection><collection>Continental Europe Database</collection><collection>Natural Science Collection</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>ProQuest Central Student</collection><collection>SciTech Premium Collection</collection><collection>ProQuest Biological Science Collection</collection><collection>Science Database</collection><collection>Biological Science Database</collection><collection>ProQuest - Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>ProQuest Central Basic</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Beilstein journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Boelke, Andreas</au><au>Finkbeiner, Peter</au><au>Nachtsheim, Boris J</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Atom-economical group-transfer reactions with hypervalent iodine compounds</atitle><jtitle>Beilstein journal of organic chemistry</jtitle><addtitle>Beilstein J Org Chem</addtitle><date>2018</date><risdate>2018</risdate><volume>14</volume><issue>1</issue><spage>1263</spage><epage>1280</epage><pages>1263-1280</pages><issn>1860-5397</issn><issn>2195-951X</issn><eissn>1860-5397</eissn><abstract>Hypervalent iodine compounds, in particular aryl-λ -iodanes, have been used extensively as electrophilic group-transfer reagents. Even though these compounds are superior substrates in terms of reactivity and stability, their utilization is accompanied by stoichiometric amounts of an aryl iodide as waste. This highly nonpolar side product can be tedious to separate from the desired target molecules and significantly reduces the overall atom efficiency of these transformations. In this short review, we want to give a brief summary of recently developed methods, in which this arising former waste is used as an additional reagent in cascade transformations to generate multiple substituted products in one step and with high atom efficiency.</abstract><cop>Germany</cop><pub>Beilstein-Institut zur Föerderung der Chemischen Wissenschaften</pub><pmid>29977394</pmid><doi>10.3762/bjoc.14.108</doi><tpages>18</tpages><orcidid>https://orcid.org/0000-0002-3759-2770</orcidid><oa>free_for_read</oa></addata></record>
fulltext fulltext
identifier ISSN: 1860-5397
ispartof Beilstein journal of organic chemistry, 2018, Vol.14 (1), p.1263-1280
issn 1860-5397
2195-951X
1860-5397
language eng
recordid cdi_doaj_primary_oai_doaj_org_article_cc0c60adaabc4e71a20a91d47185935e
source Open Access: PubMed Central; ProQuest - Publicly Available Content Database
subjects atom economy
benziodoxolones
Chemical reactions
Chemistry
homogeneous catalysis
hypervalent iodine
Iodine
Iodine compounds
iodonium salts
Ligands
Review
title Atom-economical group-transfer reactions with hypervalent iodine compounds
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-11T08%3A25%3A17IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_doaj_&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Atom-economical%20group-transfer%20reactions%20with%20hypervalent%20iodine%20compounds&rft.jtitle=Beilstein%20journal%20of%20organic%20chemistry&rft.au=Boelke,%20Andreas&rft.date=2018&rft.volume=14&rft.issue=1&rft.spage=1263&rft.epage=1280&rft.pages=1263-1280&rft.issn=1860-5397&rft.eissn=1860-5397&rft_id=info:doi/10.3762/bjoc.14.108&rft_dat=%3Cproquest_doaj_%3E2080459236%3C/proquest_doaj_%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c475t-6e0f7755b493054495d458c35e90fbb6d8c81b5776fd987c0da462cd389f0dbe3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2080459236&rft_id=info:pmid/29977394&rfr_iscdi=true