Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H‑Benzo[d][1,3]oxazin-4-ones and 4‑Benzylidene-2-aryloxazol-5(4H)‑ones
Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both d...
Gespeichert in:
Veröffentlicht in: | ACS catalysis 2016-06, Vol.6 (6), p.4010-4016 |
---|---|
Hauptverfasser: | , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
container_end_page | 4016 |
---|---|
container_issue | 6 |
container_start_page | 4010 |
container_title | ACS catalysis |
container_volume | 6 |
creator | Wang, Long Xie, Yi-Bi Huang, Nian-Yu Yan, Jia-Ying Hu, Wei-Min Liu, Ming-Guo Ding, Ming-Wu |
description | Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation. |
doi_str_mv | 10.1021/acscatal.6b00165 |
format | Article |
fullrecord | <record><control><sourceid>acs</sourceid><recordid>TN_cdi_acs_journals_10_1021_acscatal_6b00165</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c596504420</sourcerecordid><originalsourceid>FETCH-LOGICAL-a192t-eec817147555cbc58637652869f864511936b3307a5bd538eaeb732d123fffdf3</originalsourceid><addsrcrecordid>eNpNkMtKAzEUhoMoWGr3LrNUaGoyyclMl7VYKxQEL7goZcjkYlOGBGZGcLryFfQRfRJnsIJn85_Fd_4DH0LnjE4YTdiV0rVWjSonsqCUSThCg4QBEBAcjv_tp2hU1zvajQCZpXSAvub9Xdt4jdVekRffNP4VP1ilGx8Djg7PtDd4Fratqbyx2MUKN1uLH9vQRe3rnhHL74_Paxv2cW02azbmm_iu9j4QQWKwNVbBYHFA2rKrCZYkRFVt2XOxJHAhlpcd0NNn6MSpsrajQw7R8-Lmab4kq_vbu_lsRRSbJg2xVmcsZSIFAF1oyCRPJSSZnLpMCmBsymXBOU0VFAZ4ZpUtUp4YlnDnnHF8iMa_vZ29fBffqtB9yxnNe6X5n9L8oJT_AOJBbmE</addsrcrecordid><sourcetype>Publisher</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H‑Benzo[d][1,3]oxazin-4-ones and 4‑Benzylidene-2-aryloxazol-5(4H)‑ones</title><source>American Chemical Society Journals</source><creator>Wang, Long ; Xie, Yi-Bi ; Huang, Nian-Yu ; Yan, Jia-Ying ; Hu, Wei-Min ; Liu, Ming-Guo ; Ding, Ming-Wu</creator><creatorcontrib>Wang, Long ; Xie, Yi-Bi ; Huang, Nian-Yu ; Yan, Jia-Ying ; Hu, Wei-Min ; Liu, Ming-Guo ; Ding, Ming-Wu</creatorcontrib><description>Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation.</description><identifier>ISSN: 2155-5435</identifier><identifier>EISSN: 2155-5435</identifier><identifier>DOI: 10.1021/acscatal.6b00165</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>ACS catalysis, 2016-06, Vol.6 (6), p.4010-4016</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acscatal.6b00165$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acscatal.6b00165$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,27076,27924,27925,56738,56788</link.rule.ids></links><search><creatorcontrib>Wang, Long</creatorcontrib><creatorcontrib>Xie, Yi-Bi</creatorcontrib><creatorcontrib>Huang, Nian-Yu</creatorcontrib><creatorcontrib>Yan, Jia-Ying</creatorcontrib><creatorcontrib>Hu, Wei-Min</creatorcontrib><creatorcontrib>Liu, Ming-Guo</creatorcontrib><creatorcontrib>Ding, Ming-Wu</creatorcontrib><title>Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H‑Benzo[d][1,3]oxazin-4-ones and 4‑Benzylidene-2-aryloxazol-5(4H)‑ones</title><title>ACS catalysis</title><addtitle>ACS Catal</addtitle><description>Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation.</description><issn>2155-5435</issn><issn>2155-5435</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNpNkMtKAzEUhoMoWGr3LrNUaGoyyclMl7VYKxQEL7goZcjkYlOGBGZGcLryFfQRfRJnsIJn85_Fd_4DH0LnjE4YTdiV0rVWjSonsqCUSThCg4QBEBAcjv_tp2hU1zvajQCZpXSAvub9Xdt4jdVekRffNP4VP1ilGx8Djg7PtDd4Fratqbyx2MUKN1uLH9vQRe3rnhHL74_Paxv2cW02azbmm_iu9j4QQWKwNVbBYHFA2rKrCZYkRFVt2XOxJHAhlpcd0NNn6MSpsrajQw7R8-Lmab4kq_vbu_lsRRSbJg2xVmcsZSIFAF1oyCRPJSSZnLpMCmBsymXBOU0VFAZ4ZpUtUp4YlnDnnHF8iMa_vZ29fBffqtB9yxnNe6X5n9L8oJT_AOJBbmE</recordid><startdate>20160603</startdate><enddate>20160603</enddate><creator>Wang, Long</creator><creator>Xie, Yi-Bi</creator><creator>Huang, Nian-Yu</creator><creator>Yan, Jia-Ying</creator><creator>Hu, Wei-Min</creator><creator>Liu, Ming-Guo</creator><creator>Ding, Ming-Wu</creator><general>American Chemical Society</general><scope/></search><sort><creationdate>20160603</creationdate><title>Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H‑Benzo[d][1,3]oxazin-4-ones and 4‑Benzylidene-2-aryloxazol-5(4H)‑ones</title><author>Wang, Long ; Xie, Yi-Bi ; Huang, Nian-Yu ; Yan, Jia-Ying ; Hu, Wei-Min ; Liu, Ming-Guo ; Ding, Ming-Wu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a192t-eec817147555cbc58637652869f864511936b3307a5bd538eaeb732d123fffdf3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Wang, Long</creatorcontrib><creatorcontrib>Xie, Yi-Bi</creatorcontrib><creatorcontrib>Huang, Nian-Yu</creatorcontrib><creatorcontrib>Yan, Jia-Ying</creatorcontrib><creatorcontrib>Hu, Wei-Min</creatorcontrib><creatorcontrib>Liu, Ming-Guo</creatorcontrib><creatorcontrib>Ding, Ming-Wu</creatorcontrib><jtitle>ACS catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Wang, Long</au><au>Xie, Yi-Bi</au><au>Huang, Nian-Yu</au><au>Yan, Jia-Ying</au><au>Hu, Wei-Min</au><au>Liu, Ming-Guo</au><au>Ding, Ming-Wu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H‑Benzo[d][1,3]oxazin-4-ones and 4‑Benzylidene-2-aryloxazol-5(4H)‑ones</atitle><jtitle>ACS catalysis</jtitle><addtitle>ACS Catal</addtitle><date>2016-06-03</date><risdate>2016</risdate><volume>6</volume><issue>6</issue><spage>4010</spage><epage>4016</epage><pages>4010-4016</pages><issn>2155-5435</issn><eissn>2155-5435</eissn><abstract>Compared to the aza-Wittig reaction of aldehydes, ketones, amides, and esters, the aza-Wittig reaction of acid anhydride was always overlooked, which should be an important part of Wittig reactions. Here, the aza-Wittig reaction of anhydride and catalytic aza-Wittig reaction of anhydride were both developed with high yields, which provides an efficient method to synthesize of 4H-benzo[d][1,3]oxazin-4-ones and 4-benzylidene-2-aryloxazol-5(4H)-ones. The strategy of copper-catalyzed reduction of phosphine oxide was used and found effective for this transformation. Additionally, the one-pot catalytic aza-Wittig reaction of carboxylic acids was achieved. Furthermore, NMR experiments and Hammett plot recorded the process of catalytic aza-Wittig reaction of anhydride, which provides direct proof that the copper-catalyzed reduction of waste phosphine oxide is the key step in this transformation.</abstract><pub>American Chemical Society</pub><doi>10.1021/acscatal.6b00165</doi><tpages>7</tpages></addata></record> |
fulltext | fulltext |
identifier | ISSN: 2155-5435 |
ispartof | ACS catalysis, 2016-06, Vol.6 (6), p.4010-4016 |
issn | 2155-5435 2155-5435 |
language | eng |
recordid | cdi_acs_journals_10_1021_acscatal_6b00165 |
source | American Chemical Society Journals |
title | Catalytic aza-Wittig Reaction of Acid Anhydride for the Synthesis of 4H‑Benzo[d][1,3]oxazin-4-ones and 4‑Benzylidene-2-aryloxazol-5(4H)‑ones |
url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-25T00%3A10%3A36IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-acs&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Catalytic%20aza-Wittig%20Reaction%20of%20Acid%20Anhydride%20for%20the%20Synthesis%20of%204H%E2%80%91Benzo%5Bd%5D%5B1,3%5Doxazin-4-ones%20and%204%E2%80%91Benzylidene-2-aryloxazol-5(4H)%E2%80%91ones&rft.jtitle=ACS%20catalysis&rft.au=Wang,%20Long&rft.date=2016-06-03&rft.volume=6&rft.issue=6&rft.spage=4010&rft.epage=4016&rft.pages=4010-4016&rft.issn=2155-5435&rft.eissn=2155-5435&rft_id=info:doi/10.1021/acscatal.6b00165&rft_dat=%3Cacs%3Ec596504420%3C/acs%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 |