Synthesis of Siloxane Derivatives of Phenylboronic Acids of Different Structures
The synthesis of a storage-stable organosilicon modifier with a dioxaborolane-protecting group is described. Its high reactivity and selective anti-Markovnikov addition in hydrosilylation reactions to afford siloxanes of various structures are shown. The possibility of deprotection of both the initi...
Gespeichert in:
| Veröffentlicht in: | Journal of organic chemistry 2023-07, Vol.88 (13), p.8583-8599 |
|---|---|
| Hauptverfasser: | , , , , , , |
| Format: | Artikel |
| Sprache: | eng |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 8599 |
|---|---|
| container_issue | 13 |
| container_start_page | 8583 |
| container_title | Journal of organic chemistry |
| container_volume | 88 |
| creator | Manokhina, Elizaveta A. Anisimov, Anton A. Drozdov, Fedor V. Tukhvatshin, Rinat S. Peregudov, Alexander S. Aksenova, Svetlana A. Muzafarov, Aziz M. |
| description | The synthesis of a storage-stable organosilicon modifier with a dioxaborolane-protecting group is described. Its high reactivity and selective anti-Markovnikov addition in hydrosilylation reactions to afford siloxanes of various structures are shown. The possibility of deprotection of both the initial modifier and its siloxane derivatives under mild conditions using water in yields up to 96% is demonstrated. The existence of an equilibrium between the organosilicon derivatives of phenylboronic acids and their cyclic six-membered boroxines was confirmed by 1H NMR spectroscopy and X-ray diffraction analysis data. The use of siloxane derivatives of phenylboronic acids in Suzuki–Miyaura and Chan–Lam cross-coupling reactions was studied. All synthesized compounds were characterized by NMR (1H, 11B, 13C, and 29Si), IR spectroscopy, and high-resolution mass spectrometry. |
| doi_str_mv | 10.1021/acs.joc.3c00504 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2822374659</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2822374659</sourcerecordid><originalsourceid>FETCH-LOGICAL-a287t-387c3bc3167a69f2ba2baaff088817cdad3ad2651d6da9d93a1739a89cc8ece83</originalsourceid><addsrcrecordid>eNp1kF1LwzAUhoMobk6vvZNeCtItH02aXo7NLxg4mF6HNElZRtfMpB3u3xvX6Z3hQODwnJdzHgBuERwjiNFEqjDeODUmCkIKszMwRBTDlBUwOwdDCDFOCWZkAK5C2MD4KKWXYEByzDKasSFYrg5NuzbBhsRVycrW7ks2Jpkbb_eytXtz7C_XpjnUpfOusSqZKquP7bmtKuNN0yar1neq7bwJ1-CiknUwN6d_BD6eHt9nL-ni7fl1Nl2kEvO8TQnPFSkVQSyXrKhwKWPJqoKcc5QrLTWRGjOKNNOy0AWRKCeF5IVS3CjDyQjc97k77z47E1qxtUGZuo7ruy4IzDEmecZoEdFJjyrvQvCmEjtvt9IfBILiR6OIGkXUKE4a48TdKbwrt0b_8b_eIvDQA_1k55t4679x3_vqfs4</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2822374659</pqid></control><display><type>article</type><title>Synthesis of Siloxane Derivatives of Phenylboronic Acids of Different Structures</title><source>ACS Publications</source><creator>Manokhina, Elizaveta A. ; Anisimov, Anton A. ; Drozdov, Fedor V. ; Tukhvatshin, Rinat S. ; Peregudov, Alexander S. ; Aksenova, Svetlana A. ; Muzafarov, Aziz M.</creator><creatorcontrib>Manokhina, Elizaveta A. ; Anisimov, Anton A. ; Drozdov, Fedor V. ; Tukhvatshin, Rinat S. ; Peregudov, Alexander S. ; Aksenova, Svetlana A. ; Muzafarov, Aziz M.</creatorcontrib><description>The synthesis of a storage-stable organosilicon modifier with a dioxaborolane-protecting group is described. Its high reactivity and selective anti-Markovnikov addition in hydrosilylation reactions to afford siloxanes of various structures are shown. The possibility of deprotection of both the initial modifier and its siloxane derivatives under mild conditions using water in yields up to 96% is demonstrated. The existence of an equilibrium between the organosilicon derivatives of phenylboronic acids and their cyclic six-membered boroxines was confirmed by 1H NMR spectroscopy and X-ray diffraction analysis data. The use of siloxane derivatives of phenylboronic acids in Suzuki–Miyaura and Chan–Lam cross-coupling reactions was studied. All synthesized compounds were characterized by NMR (1H, 11B, 13C, and 29Si), IR spectroscopy, and high-resolution mass spectrometry.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.3c00504</identifier><identifier>PMID: 37264546</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2023-07, Vol.88 (13), p.8583-8599</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-a287t-387c3bc3167a69f2ba2baaff088817cdad3ad2651d6da9d93a1739a89cc8ece83</cites><orcidid>0009-0008-3184-6347 ; 0000-0003-2611-464X ; 0000-0001-7062-5012</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.joc.3c00504$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.3c00504$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,2763,27075,27923,27924,56737,56787</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37264546$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Manokhina, Elizaveta A.</creatorcontrib><creatorcontrib>Anisimov, Anton A.</creatorcontrib><creatorcontrib>Drozdov, Fedor V.</creatorcontrib><creatorcontrib>Tukhvatshin, Rinat S.</creatorcontrib><creatorcontrib>Peregudov, Alexander S.</creatorcontrib><creatorcontrib>Aksenova, Svetlana A.</creatorcontrib><creatorcontrib>Muzafarov, Aziz M.</creatorcontrib><title>Synthesis of Siloxane Derivatives of Phenylboronic Acids of Different Structures</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The synthesis of a storage-stable organosilicon modifier with a dioxaborolane-protecting group is described. Its high reactivity and selective anti-Markovnikov addition in hydrosilylation reactions to afford siloxanes of various structures are shown. The possibility of deprotection of both the initial modifier and its siloxane derivatives under mild conditions using water in yields up to 96% is demonstrated. The existence of an equilibrium between the organosilicon derivatives of phenylboronic acids and their cyclic six-membered boroxines was confirmed by 1H NMR spectroscopy and X-ray diffraction analysis data. The use of siloxane derivatives of phenylboronic acids in Suzuki–Miyaura and Chan–Lam cross-coupling reactions was studied. All synthesized compounds were characterized by NMR (1H, 11B, 13C, and 29Si), IR spectroscopy, and high-resolution mass spectrometry.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp1kF1LwzAUhoMobk6vvZNeCtItH02aXo7NLxg4mF6HNElZRtfMpB3u3xvX6Z3hQODwnJdzHgBuERwjiNFEqjDeODUmCkIKszMwRBTDlBUwOwdDCDFOCWZkAK5C2MD4KKWXYEByzDKasSFYrg5NuzbBhsRVycrW7ks2Jpkbb_eytXtz7C_XpjnUpfOusSqZKquP7bmtKuNN0yar1neq7bwJ1-CiknUwN6d_BD6eHt9nL-ni7fl1Nl2kEvO8TQnPFSkVQSyXrKhwKWPJqoKcc5QrLTWRGjOKNNOy0AWRKCeF5IVS3CjDyQjc97k77z47E1qxtUGZuo7ruy4IzDEmecZoEdFJjyrvQvCmEjtvt9IfBILiR6OIGkXUKE4a48TdKbwrt0b_8b_eIvDQA_1k55t4679x3_vqfs4</recordid><startdate>20230707</startdate><enddate>20230707</enddate><creator>Manokhina, Elizaveta A.</creator><creator>Anisimov, Anton A.</creator><creator>Drozdov, Fedor V.</creator><creator>Tukhvatshin, Rinat S.</creator><creator>Peregudov, Alexander S.</creator><creator>Aksenova, Svetlana A.</creator><creator>Muzafarov, Aziz M.</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0009-0008-3184-6347</orcidid><orcidid>https://orcid.org/0000-0003-2611-464X</orcidid><orcidid>https://orcid.org/0000-0001-7062-5012</orcidid></search><sort><creationdate>20230707</creationdate><title>Synthesis of Siloxane Derivatives of Phenylboronic Acids of Different Structures</title><author>Manokhina, Elizaveta A. ; Anisimov, Anton A. ; Drozdov, Fedor V. ; Tukhvatshin, Rinat S. ; Peregudov, Alexander S. ; Aksenova, Svetlana A. ; Muzafarov, Aziz M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a287t-387c3bc3167a69f2ba2baaff088817cdad3ad2651d6da9d93a1739a89cc8ece83</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Manokhina, Elizaveta A.</creatorcontrib><creatorcontrib>Anisimov, Anton A.</creatorcontrib><creatorcontrib>Drozdov, Fedor V.</creatorcontrib><creatorcontrib>Tukhvatshin, Rinat S.</creatorcontrib><creatorcontrib>Peregudov, Alexander S.</creatorcontrib><creatorcontrib>Aksenova, Svetlana A.</creatorcontrib><creatorcontrib>Muzafarov, Aziz M.</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Manokhina, Elizaveta A.</au><au>Anisimov, Anton A.</au><au>Drozdov, Fedor V.</au><au>Tukhvatshin, Rinat S.</au><au>Peregudov, Alexander S.</au><au>Aksenova, Svetlana A.</au><au>Muzafarov, Aziz M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Siloxane Derivatives of Phenylboronic Acids of Different Structures</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2023-07-07</date><risdate>2023</risdate><volume>88</volume><issue>13</issue><spage>8583</spage><epage>8599</epage><pages>8583-8599</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>The synthesis of a storage-stable organosilicon modifier with a dioxaborolane-protecting group is described. Its high reactivity and selective anti-Markovnikov addition in hydrosilylation reactions to afford siloxanes of various structures are shown. The possibility of deprotection of both the initial modifier and its siloxane derivatives under mild conditions using water in yields up to 96% is demonstrated. The existence of an equilibrium between the organosilicon derivatives of phenylboronic acids and their cyclic six-membered boroxines was confirmed by 1H NMR spectroscopy and X-ray diffraction analysis data. The use of siloxane derivatives of phenylboronic acids in Suzuki–Miyaura and Chan–Lam cross-coupling reactions was studied. All synthesized compounds were characterized by NMR (1H, 11B, 13C, and 29Si), IR spectroscopy, and high-resolution mass spectrometry.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>37264546</pmid><doi>10.1021/acs.joc.3c00504</doi><tpages>17</tpages><orcidid>https://orcid.org/0009-0008-3184-6347</orcidid><orcidid>https://orcid.org/0000-0003-2611-464X</orcidid><orcidid>https://orcid.org/0000-0001-7062-5012</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0022-3263 |
| ispartof | Journal of organic chemistry, 2023-07, Vol.88 (13), p.8583-8599 |
| issn | 0022-3263 1520-6904 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_2822374659 |
| source | ACS Publications |
| title | Synthesis of Siloxane Derivatives of Phenylboronic Acids of Different Structures |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-13T02%3A40%3A50IST&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=Synthesis%20of%20Siloxane%20Derivatives%20of%20Phenylboronic%20Acids%20of%20Different%20Structures&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Manokhina,%20Elizaveta%20A.&rft.date=2023-07-07&rft.volume=88&rft.issue=13&rft.spage=8583&rft.epage=8599&rft.pages=8583-8599&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.3c00504&rft_dat=%3Cproquest_cross%3E2822374659%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=2822374659&rft_id=info:pmid/37264546&rfr_iscdi=true |