Synthesis of Benzyltributylstannanes by the Reaction of N‑Tosylhydrazones with Bu3SnH

An efficient stannylation process with N-tosylhydrazones or directly with carbonyl compounds has been developed. A series of functionalized benzyl- and alkyltributylstannanes can be synthesized in moderate to good yields under transition-metal-free conditions. Tandem transformations involving stanny...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Journal of organic chemistry 2017-01, Vol.82 (1), p.624-632
Hauptverfasser: Qiu, Di, Wang, Shuai, Meng, He, Tang, Shengbo, Zhang, Yan, Wang, Jianbo
Format: Artikel
Sprache:eng
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 632
container_issue 1
container_start_page 624
container_title Journal of organic chemistry
container_volume 82
creator Qiu, Di
Wang, Shuai
Meng, He
Tang, Shengbo
Zhang, Yan
Wang, Jianbo
description An efficient stannylation process with N-tosylhydrazones or directly with carbonyl compounds has been developed. A series of functionalized benzyl- and alkyltributylstannanes can be synthesized in moderate to good yields under transition-metal-free conditions. Tandem transformations involving stannylation/Stille cross-coupling reaction have been carried out without purification of the benzyltributylstannane intermediates to afford a series of diarylmethane derivatives.
doi_str_mv 10.1021/acs.joc.6b02639
format Article
fullrecord <record><control><sourceid>proquest_acs_j</sourceid><recordid>TN_cdi_proquest_miscellaneous_1852679279</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>1852679279</sourcerecordid><originalsourceid>FETCH-LOGICAL-a224t-41786a141e83f7205f4b00d00434c7794f60f3941871d5edd19f2cf40445c50c3</originalsourceid><addsrcrecordid>eNotkM1Kw0AURgdRsFbXbrMUJPXOX5JZ2mKtUBRsxWWYTGZoSpzRzARJV76Cr-iTOKW9mwv3O1w-DkLXGCYYCL6Tyk-2Tk2yCkhGxQkaYU4gzQSwUzQCICSlMThHF95vIQ7nfITeV4MNG-0bnziTTLXdDW3omqoPQ-uDtFZa7ZNqSCKUvGqpQuPsHn3--_ldOz-0m6Hu5M7tse8mbJJpT1d2cYnOjGy9vjruMXqbP6xni3T58vg0u1-mkhAWUobzIpOYYV1QkxPghlUANQCjTOW5YCYDQwXDRY5rrusaC0OUYcAYVxwUHaObw9_Pzn312ofyo_FKt23s7Xpf4oKTLBckFxG9PaDRVLl1fWdjsRJDuddXHo6qPOqj_7cDZRo</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1852679279</pqid></control><display><type>article</type><title>Synthesis of Benzyltributylstannanes by the Reaction of N‑Tosylhydrazones with Bu3SnH</title><source>ACS Publications</source><creator>Qiu, Di ; Wang, Shuai ; Meng, He ; Tang, Shengbo ; Zhang, Yan ; Wang, Jianbo</creator><creatorcontrib>Qiu, Di ; Wang, Shuai ; Meng, He ; Tang, Shengbo ; Zhang, Yan ; Wang, Jianbo</creatorcontrib><description>An efficient stannylation process with N-tosylhydrazones or directly with carbonyl compounds has been developed. A series of functionalized benzyl- and alkyltributylstannanes can be synthesized in moderate to good yields under transition-metal-free conditions. Tandem transformations involving stannylation/Stille cross-coupling reaction have been carried out without purification of the benzyltributylstannane intermediates to afford a series of diarylmethane derivatives.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/acs.joc.6b02639</identifier><language>eng</language><publisher>American Chemical Society</publisher><ispartof>Journal of organic chemistry, 2017-01, Vol.82 (1), p.624-632</ispartof><rights>Copyright © 2016 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-0092-0937</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.6b02639$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.joc.6b02639$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,27081,27929,27930,56743,56793</link.rule.ids></links><search><creatorcontrib>Qiu, Di</creatorcontrib><creatorcontrib>Wang, Shuai</creatorcontrib><creatorcontrib>Meng, He</creatorcontrib><creatorcontrib>Tang, Shengbo</creatorcontrib><creatorcontrib>Zhang, Yan</creatorcontrib><creatorcontrib>Wang, Jianbo</creatorcontrib><title>Synthesis of Benzyltributylstannanes by the Reaction of N‑Tosylhydrazones with Bu3SnH</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>An efficient stannylation process with N-tosylhydrazones or directly with carbonyl compounds has been developed. A series of functionalized benzyl- and alkyltributylstannanes can be synthesized in moderate to good yields under transition-metal-free conditions. Tandem transformations involving stannylation/Stille cross-coupling reaction have been carried out without purification of the benzyltributylstannane intermediates to afford a series of diarylmethane derivatives.</description><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNotkM1Kw0AURgdRsFbXbrMUJPXOX5JZ2mKtUBRsxWWYTGZoSpzRzARJV76Cr-iTOKW9mwv3O1w-DkLXGCYYCL6Tyk-2Tk2yCkhGxQkaYU4gzQSwUzQCICSlMThHF95vIQ7nfITeV4MNG-0bnziTTLXdDW3omqoPQ-uDtFZa7ZNqSCKUvGqpQuPsHn3--_ldOz-0m6Hu5M7tse8mbJJpT1d2cYnOjGy9vjruMXqbP6xni3T58vg0u1-mkhAWUobzIpOYYV1QkxPghlUANQCjTOW5YCYDQwXDRY5rrusaC0OUYcAYVxwUHaObw9_Pzn312ofyo_FKt23s7Xpf4oKTLBckFxG9PaDRVLl1fWdjsRJDuddXHo6qPOqj_7cDZRo</recordid><startdate>20170106</startdate><enddate>20170106</enddate><creator>Qiu, Di</creator><creator>Wang, Shuai</creator><creator>Meng, He</creator><creator>Tang, Shengbo</creator><creator>Zhang, Yan</creator><creator>Wang, Jianbo</creator><general>American Chemical Society</general><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-0092-0937</orcidid></search><sort><creationdate>20170106</creationdate><title>Synthesis of Benzyltributylstannanes by the Reaction of N‑Tosylhydrazones with Bu3SnH</title><author>Qiu, Di ; Wang, Shuai ; Meng, He ; Tang, Shengbo ; Zhang, Yan ; Wang, Jianbo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a224t-41786a141e83f7205f4b00d00434c7794f60f3941871d5edd19f2cf40445c50c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Qiu, Di</creatorcontrib><creatorcontrib>Wang, Shuai</creatorcontrib><creatorcontrib>Meng, He</creatorcontrib><creatorcontrib>Tang, Shengbo</creatorcontrib><creatorcontrib>Zhang, Yan</creatorcontrib><creatorcontrib>Wang, Jianbo</creatorcontrib><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Qiu, Di</au><au>Wang, Shuai</au><au>Meng, He</au><au>Tang, Shengbo</au><au>Zhang, Yan</au><au>Wang, Jianbo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Benzyltributylstannanes by the Reaction of N‑Tosylhydrazones with Bu3SnH</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2017-01-06</date><risdate>2017</risdate><volume>82</volume><issue>1</issue><spage>624</spage><epage>632</epage><pages>624-632</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><abstract>An efficient stannylation process with N-tosylhydrazones or directly with carbonyl compounds has been developed. A series of functionalized benzyl- and alkyltributylstannanes can be synthesized in moderate to good yields under transition-metal-free conditions. Tandem transformations involving stannylation/Stille cross-coupling reaction have been carried out without purification of the benzyltributylstannane intermediates to afford a series of diarylmethane derivatives.</abstract><pub>American Chemical Society</pub><doi>10.1021/acs.joc.6b02639</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-0092-0937</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 0022-3263
ispartof Journal of organic chemistry, 2017-01, Vol.82 (1), p.624-632
issn 0022-3263
1520-6904
language eng
recordid cdi_proquest_miscellaneous_1852679279
source ACS Publications
title Synthesis of Benzyltributylstannanes by the Reaction of N‑Tosylhydrazones with Bu3SnH
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-12T19%3A37%3A20IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_acs_j&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20of%20Benzyltributylstannanes%20by%20the%20Reaction%20of%20N%E2%80%91Tosylhydrazones%20with%20Bu3SnH&rft.jtitle=Journal%20of%20organic%20chemistry&rft.au=Qiu,%20Di&rft.date=2017-01-06&rft.volume=82&rft.issue=1&rft.spage=624&rft.epage=632&rft.pages=624-632&rft.issn=0022-3263&rft.eissn=1520-6904&rft_id=info:doi/10.1021/acs.joc.6b02639&rft_dat=%3Cproquest_acs_j%3E1852679279%3C/proquest_acs_j%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=1852679279&rft_id=info:pmid/&rfr_iscdi=true