Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with -quinone methides under metal- and additive-free conditions
We report, for the first time, a visible-light-promoted tandem ring opening/1,6-conjugate addition of cyclobutanols with p -quinone methides. This transformation proceeded smoothly in the presence of an organic photocatalyst [Mes-Acr-Me] + BF 4 − , affording a series of δ,δ-diaryl ketones in moderat...
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| Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2024-02, Vol.26 (3), p.1375-138 |
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| container_title | Green chemistry : an international journal and green chemistry resource : GC |
| container_volume | 26 |
| creator | Zhou, Tongyao Zeng, Jie Liu, Yang Chen, Hang Wang, Haifeng Yan, Qiongjiao Wang, Wei Chen, Fener |
| description | We report, for the first time, a visible-light-promoted tandem ring opening/1,6-conjugate addition of cyclobutanols with
p
-quinone methides. This transformation proceeded smoothly in the presence of an organic photocatalyst [Mes-Acr-Me]
+
BF
4
−
, affording a series of δ,δ-diaryl ketones in moderate to excellent yields. Notably, this practical reaction occurs under metal- and additive-free conditions and exhibits broad substrate scope and good functional group tolerance. Moreover, DFT calculations showed that the substrate
p
-quinone methides as Brønsted bases were significant to this transformation, which could activate the transient radical cations to form the key alkoxy radical intermediates.
A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with
p
-quinone methides was developed. This protocol allowed the formation of δ,δ-diaryl ketones in the presence of a readily available organic photocatalyst. |
| doi_str_mv | 10.1039/d3gc04286c |
| format | Article |
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p
-quinone methides. This transformation proceeded smoothly in the presence of an organic photocatalyst [Mes-Acr-Me]
+
BF
4
−
, affording a series of δ,δ-diaryl ketones in moderate to excellent yields. Notably, this practical reaction occurs under metal- and additive-free conditions and exhibits broad substrate scope and good functional group tolerance. Moreover, DFT calculations showed that the substrate
p
-quinone methides as Brønsted bases were significant to this transformation, which could activate the transient radical cations to form the key alkoxy radical intermediates.
A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with
p
-quinone methides was developed. This protocol allowed the formation of δ,δ-diaryl ketones in the presence of a readily available organic photocatalyst.</description><identifier>ISSN: 1463-9262</identifier><identifier>EISSN: 1463-9270</identifier><identifier>DOI: 10.1039/d3gc04286c</identifier><ispartof>Green chemistry : an international journal and green chemistry resource : GC, 2024-02, Vol.26 (3), p.1375-138</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Zhou, Tongyao</creatorcontrib><creatorcontrib>Zeng, Jie</creatorcontrib><creatorcontrib>Liu, Yang</creatorcontrib><creatorcontrib>Chen, Hang</creatorcontrib><creatorcontrib>Wang, Haifeng</creatorcontrib><creatorcontrib>Yan, Qiongjiao</creatorcontrib><creatorcontrib>Wang, Wei</creatorcontrib><creatorcontrib>Chen, Fener</creatorcontrib><title>Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with -quinone methides under metal- and additive-free conditions</title><title>Green chemistry : an international journal and green chemistry resource : GC</title><description>We report, for the first time, a visible-light-promoted tandem ring opening/1,6-conjugate addition of cyclobutanols with
p
-quinone methides. This transformation proceeded smoothly in the presence of an organic photocatalyst [Mes-Acr-Me]
+
BF
4
−
, affording a series of δ,δ-diaryl ketones in moderate to excellent yields. Notably, this practical reaction occurs under metal- and additive-free conditions and exhibits broad substrate scope and good functional group tolerance. Moreover, DFT calculations showed that the substrate
p
-quinone methides as Brønsted bases were significant to this transformation, which could activate the transient radical cations to form the key alkoxy radical intermediates.
A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with
p
-quinone methides was developed. This protocol allowed the formation of δ,δ-diaryl ketones in the presence of a readily available organic photocatalyst.</description><issn>1463-9262</issn><issn>1463-9270</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFz89KAzEQBvAgClbtpXdhHsDYZHdJ7VkUH0B6LWkyuzslm9T8UfoaPrERix49fTN8zA-GsYUU91K066VtByO65kGZMzaTnWr5ulmJ899ZNZfsKqW9EFKuVDdjnxtKtHPIHQ1j5uRtMWgha29xgkh-gHBAX3Mp7xQ3we_LoDOCtpYyBQ-hB3M0LuxKPQouwQflEfhbIR88woR5JIsJShXj96odh8qfhHfkfUSEKv-A6YZd9NolnJ_ymt0-P70-vvCYzPYQadLxuP17tP2v_wKgkFmg</recordid><startdate>20240205</startdate><enddate>20240205</enddate><creator>Zhou, Tongyao</creator><creator>Zeng, Jie</creator><creator>Liu, Yang</creator><creator>Chen, Hang</creator><creator>Wang, Haifeng</creator><creator>Yan, Qiongjiao</creator><creator>Wang, Wei</creator><creator>Chen, Fener</creator><scope/></search><sort><creationdate>20240205</creationdate><title>Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with -quinone methides under metal- and additive-free conditions</title><author>Zhou, Tongyao ; Zeng, Jie ; Liu, Yang ; Chen, Hang ; Wang, Haifeng ; Yan, Qiongjiao ; Wang, Wei ; Chen, Fener</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_d3gc04286c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><creationdate>2024</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zhou, Tongyao</creatorcontrib><creatorcontrib>Zeng, Jie</creatorcontrib><creatorcontrib>Liu, Yang</creatorcontrib><creatorcontrib>Chen, Hang</creatorcontrib><creatorcontrib>Wang, Haifeng</creatorcontrib><creatorcontrib>Yan, Qiongjiao</creatorcontrib><creatorcontrib>Wang, Wei</creatorcontrib><creatorcontrib>Chen, Fener</creatorcontrib><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Zhou, Tongyao</au><au>Zeng, Jie</au><au>Liu, Yang</au><au>Chen, Hang</au><au>Wang, Haifeng</au><au>Yan, Qiongjiao</au><au>Wang, Wei</au><au>Chen, Fener</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with -quinone methides under metal- and additive-free conditions</atitle><jtitle>Green chemistry : an international journal and green chemistry resource : GC</jtitle><date>2024-02-05</date><risdate>2024</risdate><volume>26</volume><issue>3</issue><spage>1375</spage><epage>138</epage><pages>1375-138</pages><issn>1463-9262</issn><eissn>1463-9270</eissn><abstract>We report, for the first time, a visible-light-promoted tandem ring opening/1,6-conjugate addition of cyclobutanols with
p
-quinone methides. This transformation proceeded smoothly in the presence of an organic photocatalyst [Mes-Acr-Me]
+
BF
4
−
, affording a series of δ,δ-diaryl ketones in moderate to excellent yields. Notably, this practical reaction occurs under metal- and additive-free conditions and exhibits broad substrate scope and good functional group tolerance. Moreover, DFT calculations showed that the substrate
p
-quinone methides as Brønsted bases were significant to this transformation, which could activate the transient radical cations to form the key alkoxy radical intermediates.
A visible-light-mediated tandem ring opening/1,6-conjugate addition of cyclobutanols with
p
-quinone methides was developed. This protocol allowed the formation of δ,δ-diaryl ketones in the presence of a readily available organic photocatalyst.</abstract><doi>10.1039/d3gc04286c</doi><tpages>6</tpages></addata></record> |
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| identifier | ISSN: 1463-9262 |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Visible-light-induced tandem ring opening/1,6-conjugate addition of cyclobutanols with -quinone methides under metal- and additive-free conditions |
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