Directed Magnesiation of Polyhaloaromatics using the Tetramethylpiperidylmagnesium Reagents TMP 2 Mg⋅2 LiCl and TMPMgCl⋅LiCl

A convenient and efficient functionalization of polyhaloaromatics via regioselective magnesiation has been developed. Starting from simple, inexpensive but structurally challenging arenes, metallation by magnesium amide bases was achieved under mild conditions. The desired Grignard reagents were sta...

Full description

Saved in:
Bibliographic Details
Published in:Advanced synthesis & catalysis 2013-05, Vol.355 (8), p.1553-1560
Main Authors: Unsinn, Andreas, Rohbogner, Christoph J., Knochel, Paul
Format: Article
Language:English
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-c845-2db9c41c2f9e2ca349864f2686bad47906de05cc6d040495a901f9eeb638c59b3
cites cdi_FETCH-LOGICAL-c845-2db9c41c2f9e2ca349864f2686bad47906de05cc6d040495a901f9eeb638c59b3
container_end_page 1560
container_issue 8
container_start_page 1553
container_title Advanced synthesis & catalysis
container_volume 355
creator Unsinn, Andreas
Rohbogner, Christoph J.
Knochel, Paul
description A convenient and efficient functionalization of polyhaloaromatics via regioselective magnesiation has been developed. Starting from simple, inexpensive but structurally challenging arenes, metallation by magnesium amide bases was achieved under mild conditions. The desired Grignard reagents were stable towards aryne formation, were obtained in good yields within short reaction times and could be reacted with a variety of typical electrophiles, providing attractive, functionalized building blocks in good to excellent yields. As an application we have prepared the antimicrobial natural product 2,6‐dichloro‐3‐phenethylphenol isolated from the New Zealand liverwort Riccardia marginata . This synthesis involves a mixed bimetallic compound prepared via metallation of a phenylboronic acid pinacol ester derivative and subsequent selective cross‐coupling.
doi_str_mv 10.1002/adsc.201300185
format article
fullrecord <record><control><sourceid>crossref</sourceid><recordid>TN_cdi_crossref_primary_10_1002_adsc_201300185</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>10_1002_adsc_201300185</sourcerecordid><originalsourceid>FETCH-LOGICAL-c845-2db9c41c2f9e2ca349864f2686bad47906de05cc6d040495a901f9eeb638c59b3</originalsourceid><addsrcrecordid>eNo9kM1KxDAUhYMoOI5uXecFOiZpkjZLqb8wxUG6L2mSdiJpOySdRXciuBDfcp7ElpFZ3cPHOXfxAXCL0QojRO6kDmpFEI4Rwik7AwvMMYso5uL8lBm6BFchfEyVJE2SBfh6sN6owWiYy6YzwcrB9h3sa7jp3biVrpe-byeoAtwH2zVw2BpYmMHL1gzb0e3sznirR9ce9_sWvhvZmG4IsMg3kMC8Ofx-k8Pnz9pmDspOzzxvMjfhGV2Di1q6YG7-7xIUT49F9hKt355fs_t1pFLKIqIroShWpBaGKBlTkXJaE57ySmqaCMS1QUwprhFFVDApEJ6qpuJxqpio4iVYHd8q34fgTV3uvG2lH0uMyllgOQssTwLjP89jaJs</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Directed Magnesiation of Polyhaloaromatics using the Tetramethylpiperidylmagnesium Reagents TMP 2 Mg⋅2 LiCl and TMPMgCl⋅LiCl</title><source>Wiley</source><creator>Unsinn, Andreas ; Rohbogner, Christoph J. ; Knochel, Paul</creator><creatorcontrib>Unsinn, Andreas ; Rohbogner, Christoph J. ; Knochel, Paul</creatorcontrib><description>A convenient and efficient functionalization of polyhaloaromatics via regioselective magnesiation has been developed. Starting from simple, inexpensive but structurally challenging arenes, metallation by magnesium amide bases was achieved under mild conditions. The desired Grignard reagents were stable towards aryne formation, were obtained in good yields within short reaction times and could be reacted with a variety of typical electrophiles, providing attractive, functionalized building blocks in good to excellent yields. As an application we have prepared the antimicrobial natural product 2,6‐dichloro‐3‐phenethylphenol isolated from the New Zealand liverwort Riccardia marginata . This synthesis involves a mixed bimetallic compound prepared via metallation of a phenylboronic acid pinacol ester derivative and subsequent selective cross‐coupling.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201300185</identifier><language>eng</language><ispartof>Advanced synthesis &amp; catalysis, 2013-05, Vol.355 (8), p.1553-1560</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c845-2db9c41c2f9e2ca349864f2686bad47906de05cc6d040495a901f9eeb638c59b3</citedby><cites>FETCH-LOGICAL-c845-2db9c41c2f9e2ca349864f2686bad47906de05cc6d040495a901f9eeb638c59b3</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>Unsinn, Andreas</creatorcontrib><creatorcontrib>Rohbogner, Christoph J.</creatorcontrib><creatorcontrib>Knochel, Paul</creatorcontrib><title>Directed Magnesiation of Polyhaloaromatics using the Tetramethylpiperidylmagnesium Reagents TMP 2 Mg⋅2 LiCl and TMPMgCl⋅LiCl</title><title>Advanced synthesis &amp; catalysis</title><description>A convenient and efficient functionalization of polyhaloaromatics via regioselective magnesiation has been developed. Starting from simple, inexpensive but structurally challenging arenes, metallation by magnesium amide bases was achieved under mild conditions. The desired Grignard reagents were stable towards aryne formation, were obtained in good yields within short reaction times and could be reacted with a variety of typical electrophiles, providing attractive, functionalized building blocks in good to excellent yields. As an application we have prepared the antimicrobial natural product 2,6‐dichloro‐3‐phenethylphenol isolated from the New Zealand liverwort Riccardia marginata . This synthesis involves a mixed bimetallic compound prepared via metallation of a phenylboronic acid pinacol ester derivative and subsequent selective cross‐coupling.</description><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2013</creationdate><recordtype>article</recordtype><recordid>eNo9kM1KxDAUhYMoOI5uXecFOiZpkjZLqb8wxUG6L2mSdiJpOySdRXciuBDfcp7ElpFZ3cPHOXfxAXCL0QojRO6kDmpFEI4Rwik7AwvMMYso5uL8lBm6BFchfEyVJE2SBfh6sN6owWiYy6YzwcrB9h3sa7jp3biVrpe-byeoAtwH2zVw2BpYmMHL1gzb0e3sznirR9ce9_sWvhvZmG4IsMg3kMC8Ofx-k8Pnz9pmDspOzzxvMjfhGV2Di1q6YG7-7xIUT49F9hKt355fs_t1pFLKIqIroShWpBaGKBlTkXJaE57ySmqaCMS1QUwprhFFVDApEJ6qpuJxqpio4iVYHd8q34fgTV3uvG2lH0uMyllgOQssTwLjP89jaJs</recordid><startdate>20130517</startdate><enddate>20130517</enddate><creator>Unsinn, Andreas</creator><creator>Rohbogner, Christoph J.</creator><creator>Knochel, Paul</creator><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20130517</creationdate><title>Directed Magnesiation of Polyhaloaromatics using the Tetramethylpiperidylmagnesium Reagents TMP 2 Mg⋅2 LiCl and TMPMgCl⋅LiCl</title><author>Unsinn, Andreas ; Rohbogner, Christoph J. ; Knochel, Paul</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c845-2db9c41c2f9e2ca349864f2686bad47906de05cc6d040495a901f9eeb638c59b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2013</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Unsinn, Andreas</creatorcontrib><creatorcontrib>Rohbogner, Christoph J.</creatorcontrib><creatorcontrib>Knochel, Paul</creatorcontrib><collection>CrossRef</collection><jtitle>Advanced synthesis &amp; catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Unsinn, Andreas</au><au>Rohbogner, Christoph J.</au><au>Knochel, Paul</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Directed Magnesiation of Polyhaloaromatics using the Tetramethylpiperidylmagnesium Reagents TMP 2 Mg⋅2 LiCl and TMPMgCl⋅LiCl</atitle><jtitle>Advanced synthesis &amp; catalysis</jtitle><date>2013-05-17</date><risdate>2013</risdate><volume>355</volume><issue>8</issue><spage>1553</spage><epage>1560</epage><pages>1553-1560</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A convenient and efficient functionalization of polyhaloaromatics via regioselective magnesiation has been developed. Starting from simple, inexpensive but structurally challenging arenes, metallation by magnesium amide bases was achieved under mild conditions. The desired Grignard reagents were stable towards aryne formation, were obtained in good yields within short reaction times and could be reacted with a variety of typical electrophiles, providing attractive, functionalized building blocks in good to excellent yields. As an application we have prepared the antimicrobial natural product 2,6‐dichloro‐3‐phenethylphenol isolated from the New Zealand liverwort Riccardia marginata . This synthesis involves a mixed bimetallic compound prepared via metallation of a phenylboronic acid pinacol ester derivative and subsequent selective cross‐coupling.</abstract><doi>10.1002/adsc.201300185</doi><tpages>8</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1615-4150
ispartof Advanced synthesis & catalysis, 2013-05, Vol.355 (8), p.1553-1560
issn 1615-4150
1615-4169
language eng
recordid cdi_crossref_primary_10_1002_adsc_201300185
source Wiley
title Directed Magnesiation of Polyhaloaromatics using the Tetramethylpiperidylmagnesium Reagents TMP 2 Mg⋅2 LiCl and TMPMgCl⋅LiCl
url http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-27T22%3A10%3A48IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-crossref&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Directed%20Magnesiation%20of%20Polyhaloaromatics%20using%20the%20Tetramethylpiperidylmagnesium%20Reagents%20TMP%202%20Mg%E2%8B%852%E2%80%89LiCl%20and%20TMPMgCl%E2%8B%85LiCl&rft.jtitle=Advanced%20synthesis%20&%20catalysis&rft.au=Unsinn,%20Andreas&rft.date=2013-05-17&rft.volume=355&rft.issue=8&rft.spage=1553&rft.epage=1560&rft.pages=1553-1560&rft.issn=1615-4150&rft.eissn=1615-4169&rft_id=info:doi/10.1002/adsc.201300185&rft_dat=%3Ccrossref%3E10_1002_adsc_201300185%3C/crossref%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c845-2db9c41c2f9e2ca349864f2686bad47906de05cc6d040495a901f9eeb638c59b3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true