Difunctionalization of 1,3-Butadiene via Sequential Radical Thiol-ene Reaction and Allylation by Dual Photoredox and Titanium Catalysis

Difunctionalization of 1,3-Butadiene via Sequential Radical Thiol-ene Reaction and Allylation by Dual Photoredox and Titanium Catalysis

Recently, radical difunctionalization of the feedstock 1,3-butadiene has become an attractive strategy for increasing molecular complexity. Herein, we present a novel approach that effectively combines radical thiol-ene chemistry with TiIII catalysis to enable a three-component aldehyde allylation u...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2023-07, Vol.25 (27), p.5094-5099
Hauptverfasser: Hao, Erjun, Lu, Binghui, Liu, Yonghong, Yang, Tianxiao, Yan, Huaipu, Ding, Xiaobo, Jin, Yunhe, Shi, Lei
Format: Artikel
Sprache:eng
Schlagworte:
Catalysis
Oxidation-Reduction
Sulfhydryl Compounds - chemistry
Titanium
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 5099
container_issue 27
container_start_page 5094
container_title Organic letters
container_volume 25
creator Hao, Erjun
Lu, Binghui
Liu, Yonghong
Yang, Tianxiao
Yan, Huaipu
Ding, Xiaobo
Jin, Yunhe
Shi, Lei
description Recently, radical difunctionalization of the feedstock 1,3-butadiene has become an attractive strategy for increasing molecular complexity. Herein, we present a novel approach that effectively combines radical thiol-ene chemistry with TiIII catalysis to enable a three-component aldehyde allylation using 1,3-butadiene as an allyl group source under visible light conditions. This sustainable and straightforward method has facilitated the rapid production of diverse allylic 1,3-thioalcohols with exceptional regio- and diastereoselectivity.
doi_str_mv 10.1021/acs.orglett.3c01822
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2832576623</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2832576623</sourcerecordid><originalsourceid>FETCH-LOGICAL-a345t-df077d3b1eff499b8b6d8759b0d169a65757114af802aaf67b3acff00ab4451a3</originalsourceid><addsrcrecordid>eNp9kctOwzAQRS0EgvL4AiTkJQtS_EjiZFlaXhISCMo6miQ2GDlxiR1E-QF-G5eULlnNaHTuHc1chI4pGVPC6DlUbmy7FyO9H_OK0IyxLTSiCeORIAnb3vQp2UP7zr0RQsMk30V7XPBMxIKN0PdMq76tvLYtGP0FqwZbhekZjy56D7WWrcQfGvCTfO9l6zUY_BjGVajzV21NtAIeJfx6YGhrPDFmaQancolnfSAfXq23nazt5y8x1x5a3Td4Ch7M0ml3iHYUGCeP1vUAPV9dzqc30d399e10chcBjxMf1YoIUfOSSqXiPC-zMq0zkeQlqWmaQ5qIRFAag8oIA1CpKDlUShECZRwnFPgBOh18F50N9zhfNNpV0hhope1dwTLOEpGmjAeUD2jVWec6qYpFpxvolgUlxSqBIiRQrBMo1gkE1cl6QV82st5o_l4egPMBWKnfbN-Fx7t_LX8AZ9yXFA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2832576623</pqid></control><display><type>article</type><title>Difunctionalization of 1,3-Butadiene via Sequential Radical Thiol-ene Reaction and Allylation by Dual Photoredox and Titanium Catalysis</title><source>ACS Publications</source><creator>Hao, Erjun ; Lu, Binghui ; Liu, Yonghong ; Yang, Tianxiao ; Yan, Huaipu ; Ding, Xiaobo ; Jin, Yunhe ; Shi, Lei</creator><creatorcontrib>Hao, Erjun ; Lu, Binghui ; Liu, Yonghong ; Yang, Tianxiao ; Yan, Huaipu ; Ding, Xiaobo ; Jin, Yunhe ; Shi, Lei</creatorcontrib><description>Recently, radical difunctionalization of the feedstock 1,3-butadiene has become an attractive strategy for increasing molecular complexity. Herein, we present a novel approach that effectively combines radical thiol-ene chemistry with TiIII catalysis to enable a three-component aldehyde allylation using 1,3-butadiene as an allyl group source under visible light conditions. This sustainable and straightforward method has facilitated the rapid production of diverse allylic 1,3-thioalcohols with exceptional regio- and diastereoselectivity.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/acs.orglett.3c01822</identifier><identifier>PMID: 37387472</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Oxidation-Reduction ; Sulfhydryl Compounds - chemistry ; Titanium</subject><ispartof>Organic letters, 2023-07, Vol.25 (27), p.5094-5099</ispartof><rights>2023 American Chemical Society</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a345t-df077d3b1eff499b8b6d8759b0d169a65757114af802aaf67b3acff00ab4451a3</citedby><cites>FETCH-LOGICAL-a345t-df077d3b1eff499b8b6d8759b0d169a65757114af802aaf67b3acff00ab4451a3</cites><orcidid>0000-0003-0626-4587 ; 0000-0002-2644-1168</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.orglett.3c01822$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.orglett.3c01822$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27081,27929,27930,56743,56793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/37387472$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hao, Erjun</creatorcontrib><creatorcontrib>Lu, Binghui</creatorcontrib><creatorcontrib>Liu, Yonghong</creatorcontrib><creatorcontrib>Yang, Tianxiao</creatorcontrib><creatorcontrib>Yan, Huaipu</creatorcontrib><creatorcontrib>Ding, Xiaobo</creatorcontrib><creatorcontrib>Jin, Yunhe</creatorcontrib><creatorcontrib>Shi, Lei</creatorcontrib><title>Difunctionalization of 1,3-Butadiene via Sequential Radical Thiol-ene Reaction and Allylation by Dual Photoredox and Titanium Catalysis</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>Recently, radical difunctionalization of the feedstock 1,3-butadiene has become an attractive strategy for increasing molecular complexity. Herein, we present a novel approach that effectively combines radical thiol-ene chemistry with TiIII catalysis to enable a three-component aldehyde allylation using 1,3-butadiene as an allyl group source under visible light conditions. This sustainable and straightforward method has facilitated the rapid production of diverse allylic 1,3-thioalcohols with exceptional regio- and diastereoselectivity.</description><subject>Catalysis</subject><subject>Oxidation-Reduction</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Titanium</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNp9kctOwzAQRS0EgvL4AiTkJQtS_EjiZFlaXhISCMo6miQ2GDlxiR1E-QF-G5eULlnNaHTuHc1chI4pGVPC6DlUbmy7FyO9H_OK0IyxLTSiCeORIAnb3vQp2UP7zr0RQsMk30V7XPBMxIKN0PdMq76tvLYtGP0FqwZbhekZjy56D7WWrcQfGvCTfO9l6zUY_BjGVajzV21NtAIeJfx6YGhrPDFmaQancolnfSAfXq23nazt5y8x1x5a3Td4Ch7M0ml3iHYUGCeP1vUAPV9dzqc30d399e10chcBjxMf1YoIUfOSSqXiPC-zMq0zkeQlqWmaQ5qIRFAag8oIA1CpKDlUShECZRwnFPgBOh18F50N9zhfNNpV0hhope1dwTLOEpGmjAeUD2jVWec6qYpFpxvolgUlxSqBIiRQrBMo1gkE1cl6QV82st5o_l4egPMBWKnfbN-Fx7t_LX8AZ9yXFA</recordid><startdate>20230714</startdate><enddate>20230714</enddate><creator>Hao, Erjun</creator><creator>Lu, Binghui</creator><creator>Liu, Yonghong</creator><creator>Yang, Tianxiao</creator><creator>Yan, Huaipu</creator><creator>Ding, Xiaobo</creator><creator>Jin, Yunhe</creator><creator>Shi, Lei</creator><general>American Chemical Society</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0003-0626-4587</orcidid><orcidid>https://orcid.org/0000-0002-2644-1168</orcidid></search><sort><creationdate>20230714</creationdate><title>Difunctionalization of 1,3-Butadiene via Sequential Radical Thiol-ene Reaction and Allylation by Dual Photoredox and Titanium Catalysis</title><author>Hao, Erjun ; Lu, Binghui ; Liu, Yonghong ; Yang, Tianxiao ; Yan, Huaipu ; Ding, Xiaobo ; Jin, Yunhe ; Shi, Lei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a345t-df077d3b1eff499b8b6d8759b0d169a65757114af802aaf67b3acff00ab4451a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Catalysis</topic><topic>Oxidation-Reduction</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Titanium</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hao, Erjun</creatorcontrib><creatorcontrib>Lu, Binghui</creatorcontrib><creatorcontrib>Liu, Yonghong</creatorcontrib><creatorcontrib>Yang, Tianxiao</creatorcontrib><creatorcontrib>Yan, Huaipu</creatorcontrib><creatorcontrib>Ding, Xiaobo</creatorcontrib><creatorcontrib>Jin, Yunhe</creatorcontrib><creatorcontrib>Shi, Lei</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hao, Erjun</au><au>Lu, Binghui</au><au>Liu, Yonghong</au><au>Yang, Tianxiao</au><au>Yan, Huaipu</au><au>Ding, Xiaobo</au><au>Jin, Yunhe</au><au>Shi, Lei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Difunctionalization of 1,3-Butadiene via Sequential Radical Thiol-ene Reaction and Allylation by Dual Photoredox and Titanium Catalysis</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2023-07-14</date><risdate>2023</risdate><volume>25</volume><issue>27</issue><spage>5094</spage><epage>5099</epage><pages>5094-5099</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>Recently, radical difunctionalization of the feedstock 1,3-butadiene has become an attractive strategy for increasing molecular complexity. Herein, we present a novel approach that effectively combines radical thiol-ene chemistry with TiIII catalysis to enable a three-component aldehyde allylation using 1,3-butadiene as an allyl group source under visible light conditions. This sustainable and straightforward method has facilitated the rapid production of diverse allylic 1,3-thioalcohols with exceptional regio- and diastereoselectivity.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>37387472</pmid><doi>10.1021/acs.orglett.3c01822</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0003-0626-4587</orcidid><orcidid>https://orcid.org/0000-0002-2644-1168</orcidid></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2023-07, Vol.25 (27), p.5094-5099
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_2832576623
source ACS Publications
subjects Catalysis
Oxidation-Reduction
Sulfhydryl Compounds - chemistry
Titanium
title Difunctionalization of 1,3-Butadiene via Sequential Radical Thiol-ene Reaction and Allylation by Dual Photoredox and Titanium Catalysis
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-16T12%3A59%3A42IST&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=Difunctionalization%20of%201,3-Butadiene%20via%20Sequential%20Radical%20Thiol-ene%20Reaction%20and%20Allylation%20by%20Dual%20Photoredox%20and%20Titanium%20Catalysis&rft.jtitle=Organic%20letters&rft.au=Hao,%20Erjun&rft.date=2023-07-14&rft.volume=25&rft.issue=27&rft.spage=5094&rft.epage=5099&rft.pages=5094-5099&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/acs.orglett.3c01822&rft_dat=%3Cproquest_cross%3E2832576623%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=2832576623&rft_id=info:pmid/37387472&rfr_iscdi=true