Substitution at sp 3 boron of a six-membered NHC·BH 3 : convenient access to a dihydroxyborenium cation

Substitution at sp 3 boron of a six-membered NHC·BH 3 : convenient access to a dihydroxyborenium cation

Herein, we have undertaken the synthesis and investigated the reactivity of a 6-membered saturated NHC borane adduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I led to NHC boryl iodides, 6-SIDipp·BH I (2) and 6-SIDipp·BHI (3), which were further reacted with various...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Chemical communications (Cambridge, England) England), 2022-03, Vol.58 (23), p.3783-3786
Hauptverfasser: Kundu, Gargi, Ajithkumar, V S, Raj, K Vipin, Vanka, Kumar, Tothadi, Srinu, Sen, Sakya S
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 3786
container_issue 23
container_start_page 3783
container_title Chemical communications (Cambridge, England)
container_volume 58
creator Kundu, Gargi
Ajithkumar, V S
Raj, K Vipin
Vanka, Kumar
Tothadi, Srinu
Sen, Sakya S
description Herein, we have undertaken the synthesis and investigated the reactivity of a 6-membered saturated NHC borane adduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I led to NHC boryl iodides, 6-SIDipp·BH I (2) and 6-SIDipp·BHI (3), which were further reacted with various nucleophiles to give novel 6-SIDipp based mono and disubstituted boranes with OTf (4 and 6) or ONO (5 and 7) functional groups. The addition of Br /H O to 1 smoothly results in a dihydroxyborenium cation (8).
doi_str_mv 10.1039/d1cc06816d
format Article
fullrecord <record><control><sourceid>pubmed_cross</sourceid><recordid>TN_cdi_crossref_primary_10_1039_D1CC06816D</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>35229841</sourcerecordid><originalsourceid>FETCH-LOGICAL-c991-ff52d36e64df30a7c6f45ee0c64cf3f664bc1994910a7fdeab9c320413dd8af03</originalsourceid><addsrcrecordid>eNo9kMtOwzAQRS0EolDY8AHIa6SAJ340ZgcpUKQKFnTBLnL8UINIXNkJar-MPV-GS4HZzIzu0VlchM6AXAKh8sqA1kQUIMweOgIqWMZZ8bq_vbnMJpTxETqO8Y2kAV4cohHleS4LBkdo-TLUsW_6oW98h1WP4wpTXPuQPu-wwrFZZ61taxuswU-z8uvzdpaIa6x992G7xnY9VlrbGHHvE2-a5cYEv94kR4qHFmu1dZ-gA6feoz393WO0uL9blLNs_vzwWN7MMy0lZM7x3FBhBTOOEjXRwjFuLdGCaUedEKzWICWTkEJnrKqlpjlhQI0plCN0jC52Wh18jMG6ahWaVoVNBaTatlVNoSx_2pom-HwHr4a6teYf_auHfgPR32Zr</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Substitution at sp 3 boron of a six-membered NHC·BH 3 : convenient access to a dihydroxyborenium cation</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Kundu, Gargi ; Ajithkumar, V S ; Raj, K Vipin ; Vanka, Kumar ; Tothadi, Srinu ; Sen, Sakya S</creator><creatorcontrib>Kundu, Gargi ; Ajithkumar, V S ; Raj, K Vipin ; Vanka, Kumar ; Tothadi, Srinu ; Sen, Sakya S</creatorcontrib><description>Herein, we have undertaken the synthesis and investigated the reactivity of a 6-membered saturated NHC borane adduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I led to NHC boryl iodides, 6-SIDipp·BH I (2) and 6-SIDipp·BHI (3), which were further reacted with various nucleophiles to give novel 6-SIDipp based mono and disubstituted boranes with OTf (4 and 6) or ONO (5 and 7) functional groups. The addition of Br /H O to 1 smoothly results in a dihydroxyborenium cation (8).</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d1cc06816d</identifier><identifier>PMID: 35229841</identifier><language>eng</language><publisher>England</publisher><ispartof>Chemical communications (Cambridge, England), 2022-03, Vol.58 (23), p.3783-3786</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c991-ff52d36e64df30a7c6f45ee0c64cf3f664bc1994910a7fdeab9c320413dd8af03</citedby><cites>FETCH-LOGICAL-c991-ff52d36e64df30a7c6f45ee0c64cf3f664bc1994910a7fdeab9c320413dd8af03</cites><orcidid>0000-0002-4955-5408 ; 0000-0001-6840-6937 ; 0000-0002-7178-264X ; 0000-0001-7301-7573</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/35229841$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Kundu, Gargi</creatorcontrib><creatorcontrib>Ajithkumar, V S</creatorcontrib><creatorcontrib>Raj, K Vipin</creatorcontrib><creatorcontrib>Vanka, Kumar</creatorcontrib><creatorcontrib>Tothadi, Srinu</creatorcontrib><creatorcontrib>Sen, Sakya S</creatorcontrib><title>Substitution at sp 3 boron of a six-membered NHC·BH 3 : convenient access to a dihydroxyborenium cation</title><title>Chemical communications (Cambridge, England)</title><addtitle>Chem Commun (Camb)</addtitle><description>Herein, we have undertaken the synthesis and investigated the reactivity of a 6-membered saturated NHC borane adduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I led to NHC boryl iodides, 6-SIDipp·BH I (2) and 6-SIDipp·BHI (3), which were further reacted with various nucleophiles to give novel 6-SIDipp based mono and disubstituted boranes with OTf (4 and 6) or ONO (5 and 7) functional groups. The addition of Br /H O to 1 smoothly results in a dihydroxyborenium cation (8).</description><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNo9kMtOwzAQRS0EolDY8AHIa6SAJ340ZgcpUKQKFnTBLnL8UINIXNkJar-MPV-GS4HZzIzu0VlchM6AXAKh8sqA1kQUIMweOgIqWMZZ8bq_vbnMJpTxETqO8Y2kAV4cohHleS4LBkdo-TLUsW_6oW98h1WP4wpTXPuQPu-wwrFZZ61taxuswU-z8uvzdpaIa6x992G7xnY9VlrbGHHvE2-a5cYEv94kR4qHFmu1dZ-gA6feoz393WO0uL9blLNs_vzwWN7MMy0lZM7x3FBhBTOOEjXRwjFuLdGCaUedEKzWICWTkEJnrKqlpjlhQI0plCN0jC52Wh18jMG6ahWaVoVNBaTatlVNoSx_2pom-HwHr4a6teYf_auHfgPR32Zr</recordid><startdate>20220318</startdate><enddate>20220318</enddate><creator>Kundu, Gargi</creator><creator>Ajithkumar, V S</creator><creator>Raj, K Vipin</creator><creator>Vanka, Kumar</creator><creator>Tothadi, Srinu</creator><creator>Sen, Sakya S</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-4955-5408</orcidid><orcidid>https://orcid.org/0000-0001-6840-6937</orcidid><orcidid>https://orcid.org/0000-0002-7178-264X</orcidid><orcidid>https://orcid.org/0000-0001-7301-7573</orcidid></search><sort><creationdate>20220318</creationdate><title>Substitution at sp 3 boron of a six-membered NHC·BH 3 : convenient access to a dihydroxyborenium cation</title><author>Kundu, Gargi ; Ajithkumar, V S ; Raj, K Vipin ; Vanka, Kumar ; Tothadi, Srinu ; Sen, Sakya S</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c991-ff52d36e64df30a7c6f45ee0c64cf3f664bc1994910a7fdeab9c320413dd8af03</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kundu, Gargi</creatorcontrib><creatorcontrib>Ajithkumar, V S</creatorcontrib><creatorcontrib>Raj, K Vipin</creatorcontrib><creatorcontrib>Vanka, Kumar</creatorcontrib><creatorcontrib>Tothadi, Srinu</creatorcontrib><creatorcontrib>Sen, Sakya S</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kundu, Gargi</au><au>Ajithkumar, V S</au><au>Raj, K Vipin</au><au>Vanka, Kumar</au><au>Tothadi, Srinu</au><au>Sen, Sakya S</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Substitution at sp 3 boron of a six-membered NHC·BH 3 : convenient access to a dihydroxyborenium cation</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><addtitle>Chem Commun (Camb)</addtitle><date>2022-03-18</date><risdate>2022</risdate><volume>58</volume><issue>23</issue><spage>3783</spage><epage>3786</epage><pages>3783-3786</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>Herein, we have undertaken the synthesis and investigated the reactivity of a 6-membered saturated NHC borane adduct (1). Direct electrophilic halogenation of 1 with a stoichiometric amount of I led to NHC boryl iodides, 6-SIDipp·BH I (2) and 6-SIDipp·BHI (3), which were further reacted with various nucleophiles to give novel 6-SIDipp based mono and disubstituted boranes with OTf (4 and 6) or ONO (5 and 7) functional groups. The addition of Br /H O to 1 smoothly results in a dihydroxyborenium cation (8).</abstract><cop>England</cop><pmid>35229841</pmid><doi>10.1039/d1cc06816d</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-4955-5408</orcidid><orcidid>https://orcid.org/0000-0001-6840-6937</orcidid><orcidid>https://orcid.org/0000-0002-7178-264X</orcidid><orcidid>https://orcid.org/0000-0001-7301-7573</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1359-7345
ispartof Chemical communications (Cambridge, England), 2022-03, Vol.58 (23), p.3783-3786
issn 1359-7345
1364-548X
language eng
recordid cdi_crossref_primary_10_1039_D1CC06816D
source Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
title Substitution at sp 3 boron of a six-membered NHC·BH 3 : convenient access to a dihydroxyborenium cation
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-29T00%3A50%3A10IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-pubmed_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Substitution%20at%20sp%203%20boron%20of%20a%20six-membered%20NHC%C2%B7BH%203%20:%20convenient%20access%20to%20a%20dihydroxyborenium%20cation&rft.jtitle=Chemical%20communications%20(Cambridge,%20England)&rft.au=Kundu,%20Gargi&rft.date=2022-03-18&rft.volume=58&rft.issue=23&rft.spage=3783&rft.epage=3786&rft.pages=3783-3786&rft.issn=1359-7345&rft.eissn=1364-548X&rft_id=info:doi/10.1039/d1cc06816d&rft_dat=%3Cpubmed_cross%3E35229841%3C/pubmed_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/35229841&rfr_iscdi=true