A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction

A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction

The highly exothermic nature of Reformatsky reagent formation and the reported unpredictability of the induction time for its formation pose challenging problems for scaling up Reformatsky reactions. A zinc-activation procedure using DIBAL-H was developed and investigated using reaction calorimetry...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic process research & development 2009-11, Vol.13 (6), p.1094-1099
Hauptverfasser: Girgis, Michael J, Liang, Jessica K, Du, Zhengming, Slade, Joel, Prasad, Kapa
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1099
container_issue 6
container_start_page 1094
container_title Organic process research & development
container_volume 13
creator Girgis, Michael J
Liang, Jessica K
Du, Zhengming
Slade, Joel
Prasad, Kapa
description The highly exothermic nature of Reformatsky reagent formation and the reported unpredictability of the induction time for its formation pose challenging problems for scaling up Reformatsky reactions. A zinc-activation procedure using DIBAL-H was developed and investigated using reaction calorimetry along with subsequent parts of the process. This procedure was shown to have important advantages for scale-up relative to previous zinc activation methods, including an immediate start of Reformatsky reagent formation with addition-controlled reaction. Calorimetric analysis was especially useful in specifying quickly a suitable temperature for Reformatsky reagent formation. The process was scaled up successfully.
doi_str_mv 10.1021/op900192m
format Article
fullrecord <record><control><sourceid>acs_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1021_op900192m</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>g23902746</sourcerecordid><originalsourceid>FETCH-LOGICAL-a259t-f9b7a20c0e8d8849120e4952c90abb51707ae5d2ba4712c5dc07b1c91e85e0d73</originalsourceid><addsrcrecordid>eNptkEFLw0AUhBdRsFYP_oO9ePAQfW-bzWaPsVZbCChqQbyEt5uNpKZJ2U2F_ntTKp48zRy-GYZh7BLhBkHgbbfRAKjF-oiNUAqIZJq8Hw8e0kmUYAKn7CyEFQDIBMWI5Rl_tdSQaRz_qFvLM9vX39TXXcuffWddufWOL0PdfvL7xV2WR3Net5z4i6s6v6Y-fO0GT3afOGcnFTXBXfzqmC0fZm_TeZQ_PS6mQ5aE1H1UaaNIgAWXlmkaaxTgYi2F1UDGSFSgyMlSGIoVCitLC8qg1ehS6aBUkzG7PvRa34XgXVVsfL0mvysQiv0Nxd8NA3t1YMmGYtVtfTss-4f7ARssWqo</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction</title><source>ACS Publications</source><creator>Girgis, Michael J ; Liang, Jessica K ; Du, Zhengming ; Slade, Joel ; Prasad, Kapa</creator><creatorcontrib>Girgis, Michael J ; Liang, Jessica K ; Du, Zhengming ; Slade, Joel ; Prasad, Kapa</creatorcontrib><description>The highly exothermic nature of Reformatsky reagent formation and the reported unpredictability of the induction time for its formation pose challenging problems for scaling up Reformatsky reactions. A zinc-activation procedure using DIBAL-H was developed and investigated using reaction calorimetry along with subsequent parts of the process. This procedure was shown to have important advantages for scale-up relative to previous zinc activation methods, including an immediate start of Reformatsky reagent formation with addition-controlled reaction. Calorimetric analysis was especially useful in specifying quickly a suitable temperature for Reformatsky reagent formation. The process was scaled up successfully.</description><identifier>ISSN: 1083-6160</identifier><identifier>EISSN: 1520-586X</identifier><identifier>DOI: 10.1021/op900192m</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Organic process research &amp; development, 2009-11, Vol.13 (6), p.1094-1099</ispartof><rights>Copyright © 2009 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a259t-f9b7a20c0e8d8849120e4952c90abb51707ae5d2ba4712c5dc07b1c91e85e0d73</citedby><cites>FETCH-LOGICAL-a259t-f9b7a20c0e8d8849120e4952c90abb51707ae5d2ba4712c5dc07b1c91e85e0d73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/op900192m$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/op900192m$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,2752,27053,27901,27902,56713,56763</link.rule.ids></links><search><creatorcontrib>Girgis, Michael J</creatorcontrib><creatorcontrib>Liang, Jessica K</creatorcontrib><creatorcontrib>Du, Zhengming</creatorcontrib><creatorcontrib>Slade, Joel</creatorcontrib><creatorcontrib>Prasad, Kapa</creatorcontrib><title>A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction</title><title>Organic process research &amp; development</title><addtitle>Org. Process Res. Dev</addtitle><description>The highly exothermic nature of Reformatsky reagent formation and the reported unpredictability of the induction time for its formation pose challenging problems for scaling up Reformatsky reactions. A zinc-activation procedure using DIBAL-H was developed and investigated using reaction calorimetry along with subsequent parts of the process. This procedure was shown to have important advantages for scale-up relative to previous zinc activation methods, including an immediate start of Reformatsky reagent formation with addition-controlled reaction. Calorimetric analysis was especially useful in specifying quickly a suitable temperature for Reformatsky reagent formation. The process was scaled up successfully.</description><issn>1083-6160</issn><issn>1520-586X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNptkEFLw0AUhBdRsFYP_oO9ePAQfW-bzWaPsVZbCChqQbyEt5uNpKZJ2U2F_ntTKp48zRy-GYZh7BLhBkHgbbfRAKjF-oiNUAqIZJq8Hw8e0kmUYAKn7CyEFQDIBMWI5Rl_tdSQaRz_qFvLM9vX39TXXcuffWddufWOL0PdfvL7xV2WR3Net5z4i6s6v6Y-fO0GT3afOGcnFTXBXfzqmC0fZm_TeZQ_PS6mQ5aE1H1UaaNIgAWXlmkaaxTgYi2F1UDGSFSgyMlSGIoVCitLC8qg1ehS6aBUkzG7PvRa34XgXVVsfL0mvysQiv0Nxd8NA3t1YMmGYtVtfTss-4f7ARssWqo</recordid><startdate>20091120</startdate><enddate>20091120</enddate><creator>Girgis, Michael J</creator><creator>Liang, Jessica K</creator><creator>Du, Zhengming</creator><creator>Slade, Joel</creator><creator>Prasad, Kapa</creator><general>American Chemical Society</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20091120</creationdate><title>A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction</title><author>Girgis, Michael J ; Liang, Jessica K ; Du, Zhengming ; Slade, Joel ; Prasad, Kapa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a259t-f9b7a20c0e8d8849120e4952c90abb51707ae5d2ba4712c5dc07b1c91e85e0d73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Girgis, Michael J</creatorcontrib><creatorcontrib>Liang, Jessica K</creatorcontrib><creatorcontrib>Du, Zhengming</creatorcontrib><creatorcontrib>Slade, Joel</creatorcontrib><creatorcontrib>Prasad, Kapa</creatorcontrib><collection>CrossRef</collection><jtitle>Organic process research &amp; development</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Girgis, Michael J</au><au>Liang, Jessica K</au><au>Du, Zhengming</au><au>Slade, Joel</au><au>Prasad, Kapa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction</atitle><jtitle>Organic process research &amp; development</jtitle><addtitle>Org. Process Res. Dev</addtitle><date>2009-11-20</date><risdate>2009</risdate><volume>13</volume><issue>6</issue><spage>1094</spage><epage>1099</epage><pages>1094-1099</pages><issn>1083-6160</issn><eissn>1520-586X</eissn><abstract>The highly exothermic nature of Reformatsky reagent formation and the reported unpredictability of the induction time for its formation pose challenging problems for scaling up Reformatsky reactions. A zinc-activation procedure using DIBAL-H was developed and investigated using reaction calorimetry along with subsequent parts of the process. This procedure was shown to have important advantages for scale-up relative to previous zinc activation methods, including an immediate start of Reformatsky reagent formation with addition-controlled reaction. Calorimetric analysis was especially useful in specifying quickly a suitable temperature for Reformatsky reagent formation. The process was scaled up successfully.</abstract><pub>American Chemical Society</pub><doi>10.1021/op900192m</doi><tpages>6</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1083-6160
ispartof Organic process research & development, 2009-11, Vol.13 (6), p.1094-1099
issn 1083-6160
1520-586X
language eng
recordid cdi_crossref_primary_10_1021_op900192m
source ACS Publications
title A Scalable Zinc Activation Procedure Using DIBAL-H in a Reformatsky Reaction
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T17%3A32%3A14IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Scalable%20Zinc%20Activation%20Procedure%20Using%20DIBAL-H%20in%20a%20Reformatsky%20Reaction&rft.jtitle=Organic%20process%20research%20&%20development&rft.au=Girgis,%20Michael%20J&rft.date=2009-11-20&rft.volume=13&rft.issue=6&rft.spage=1094&rft.epage=1099&rft.pages=1094-1099&rft.issn=1083-6160&rft.eissn=1520-586X&rft_id=info:doi/10.1021/op900192m&rft_dat=%3Cacs_cross%3Eg23902746%3C/acs_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_id=info:pmid/&rfr_iscdi=true