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Chiral acid-catalysed enantioselective C−H functionalization of toluene and its derivatives driven by visible light
Toluene and its derivatives are petroleum-derived raw materials produced from gasoline by catalytic reformation. These abundant chemical feedstocks are commonly used as solvents in organic synthesis. The C(sp 3 )−H functionalization of these unactivated substrates has been widely used to directly in...
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| Published in: | Nature communications 2019-04, Vol.10 (1), p.1774-1774, Article 1774 |
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| creator | Li, Fuyuan Tian, Dong Fan, Yifan Lee, Richmond Lu, Gang Yin, Yanli Qiao, Baokun Zhao, Xiaowei Xiao, Ziwei Jiang, Zhiyong |
| description | Toluene and its derivatives are petroleum-derived raw materials produced from gasoline by catalytic reformation. These abundant chemical feedstocks are commonly used as solvents in organic synthesis. The C(sp
3
)−H functionalization of these unactivated substrates has been widely used to directly introduce benzylic motifs into diverse molecules to furnish important compounds. Despite these advances, progress in asymmetric catalysis remains underdeveloped. Here, we report photoinduced radical-based enantioselective C(sp
3
)−C(sp
3
) coupling reactions of activated ketones with toluene and its derivatives by means of chiral acid catalysis. With a La(OTf)
3
/pybox complex catalyst, a variety of chiral 3-hydroxy-3-benzyl-substituted 2-oxindoles, including many conventionally difficult-to-access variants, are obtained directly from isatins in high yields with good to excellent enantioselectivities. Acenaphthoquinone is also compatible with the use of a chiral phosphoric acid (CPA) catalyst, leading to another series of important enantioenriched tertiary alcohols.
Asymmetric transformations involving abundant chemical feedstocks such as toluene and its derivatives are rather rare. Here, the authors report the radical enantioselective C(sp
3
) −C(sp
3
) coupling of activated ketones with toluenes by means of chiral acid catalysis to afford enantioenriched tertiary alcohols. |
| doi_str_mv | 10.1038/s41467-019-09857-9 |
| format | article |
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3
)−H functionalization of these unactivated substrates has been widely used to directly introduce benzylic motifs into diverse molecules to furnish important compounds. Despite these advances, progress in asymmetric catalysis remains underdeveloped. Here, we report photoinduced radical-based enantioselective C(sp
3
)−C(sp
3
) coupling reactions of activated ketones with toluene and its derivatives by means of chiral acid catalysis. With a La(OTf)
3
/pybox complex catalyst, a variety of chiral 3-hydroxy-3-benzyl-substituted 2-oxindoles, including many conventionally difficult-to-access variants, are obtained directly from isatins in high yields with good to excellent enantioselectivities. Acenaphthoquinone is also compatible with the use of a chiral phosphoric acid (CPA) catalyst, leading to another series of important enantioenriched tertiary alcohols.
Asymmetric transformations involving abundant chemical feedstocks such as toluene and its derivatives are rather rare. Here, the authors report the radical enantioselective C(sp
3
) −C(sp
3
) coupling of activated ketones with toluenes by means of chiral acid catalysis to afford enantioenriched tertiary alcohols.</description><identifier>ISSN: 2041-1723</identifier><identifier>EISSN: 2041-1723</identifier><identifier>DOI: 10.1038/s41467-019-09857-9</identifier><identifier>PMID: 30992448</identifier><language>eng</language><publisher>London: Nature Publishing Group UK</publisher><subject>119/118 ; 140/131 ; 140/146 ; 140/58 ; 639/638/439/890 ; 639/638/77/883 ; 639/638/77/888 ; Alcohols ; Catalysis ; Catalysts ; Chemical reactions ; Coupling (molecular) ; Derivatives ; Enantiomers ; Gasoline ; Humanities and Social Sciences ; Ketones ; multidisciplinary ; Organic chemistry ; Phosphoric acid ; Raw materials ; Science ; Science (multidisciplinary) ; Substrates ; Toluene</subject><ispartof>Nature communications, 2019-04, Vol.10 (1), p.1774-1774, Article 1774</ispartof><rights>The Author(s) 2019</rights><rights>The Author(s) 2019. This work is published under http://creativecommons.org/licenses/by/4.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c540t-e3f9d2d3db7250d6cfb6c7ae9207f2daa32c83decf127a386ff3e633c3cf22203</citedby><cites>FETCH-LOGICAL-c540t-e3f9d2d3db7250d6cfb6c7ae9207f2daa32c83decf127a386ff3e633c3cf22203</cites><orcidid>0000-0002-6350-7429 ; 0000-0003-1264-4914</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.proquest.com/docview/2210428483/fulltextPDF?pq-origsite=primo$$EPDF$$P50$$Gproquest$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.proquest.com/docview/2210428483?pq-origsite=primo$$EHTML$$P50$$Gproquest$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,885,25753,27924,27925,37012,37013,44590,53791,53793,75126</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/30992448$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Fuyuan</creatorcontrib><creatorcontrib>Tian, Dong</creatorcontrib><creatorcontrib>Fan, Yifan</creatorcontrib><creatorcontrib>Lee, Richmond</creatorcontrib><creatorcontrib>Lu, Gang</creatorcontrib><creatorcontrib>Yin, Yanli</creatorcontrib><creatorcontrib>Qiao, Baokun</creatorcontrib><creatorcontrib>Zhao, Xiaowei</creatorcontrib><creatorcontrib>Xiao, Ziwei</creatorcontrib><creatorcontrib>Jiang, Zhiyong</creatorcontrib><title>Chiral acid-catalysed enantioselective C−H functionalization of toluene and its derivatives driven by visible light</title><title>Nature communications</title><addtitle>Nat Commun</addtitle><addtitle>Nat Commun</addtitle><description>Toluene and its derivatives are petroleum-derived raw materials produced from gasoline by catalytic reformation. These abundant chemical feedstocks are commonly used as solvents in organic synthesis. The C(sp
3
)−H functionalization of these unactivated substrates has been widely used to directly introduce benzylic motifs into diverse molecules to furnish important compounds. Despite these advances, progress in asymmetric catalysis remains underdeveloped. Here, we report photoinduced radical-based enantioselective C(sp
3
)−C(sp
3
) coupling reactions of activated ketones with toluene and its derivatives by means of chiral acid catalysis. With a La(OTf)
3
/pybox complex catalyst, a variety of chiral 3-hydroxy-3-benzyl-substituted 2-oxindoles, including many conventionally difficult-to-access variants, are obtained directly from isatins in high yields with good to excellent enantioselectivities. Acenaphthoquinone is also compatible with the use of a chiral phosphoric acid (CPA) catalyst, leading to another series of important enantioenriched tertiary alcohols.
Asymmetric transformations involving abundant chemical feedstocks such as toluene and its derivatives are rather rare. Here, the authors report the radical enantioselective C(sp
3
) −C(sp
3
) coupling of activated ketones with toluenes by means of chiral acid catalysis to afford enantioenriched tertiary alcohols.</description><subject>119/118</subject><subject>140/131</subject><subject>140/146</subject><subject>140/58</subject><subject>639/638/439/890</subject><subject>639/638/77/883</subject><subject>639/638/77/888</subject><subject>Alcohols</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical reactions</subject><subject>Coupling (molecular)</subject><subject>Derivatives</subject><subject>Enantiomers</subject><subject>Gasoline</subject><subject>Humanities and Social Sciences</subject><subject>Ketones</subject><subject>multidisciplinary</subject><subject>Organic chemistry</subject><subject>Phosphoric acid</subject><subject>Raw materials</subject><subject>Science</subject><subject>Science 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acid-catalysed enantioselective C−H functionalization of toluene and its derivatives driven by visible light</title><author>Li, Fuyuan ; Tian, Dong ; Fan, Yifan ; Lee, Richmond ; Lu, Gang ; Yin, Yanli ; Qiao, Baokun ; Zhao, Xiaowei ; Xiao, Ziwei ; Jiang, Zhiyong</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c540t-e3f9d2d3db7250d6cfb6c7ae9207f2daa32c83decf127a386ff3e633c3cf22203</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>119/118</topic><topic>140/131</topic><topic>140/146</topic><topic>140/58</topic><topic>639/638/439/890</topic><topic>639/638/77/883</topic><topic>639/638/77/888</topic><topic>Alcohols</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical reactions</topic><topic>Coupling (molecular)</topic><topic>Derivatives</topic><topic>Enantiomers</topic><topic>Gasoline</topic><topic>Humanities and Social 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Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Nature communications</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Fuyuan</au><au>Tian, Dong</au><au>Fan, Yifan</au><au>Lee, Richmond</au><au>Lu, Gang</au><au>Yin, Yanli</au><au>Qiao, Baokun</au><au>Zhao, Xiaowei</au><au>Xiao, Ziwei</au><au>Jiang, Zhiyong</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Chiral acid-catalysed enantioselective C−H functionalization of toluene and its derivatives driven by visible light</atitle><jtitle>Nature communications</jtitle><stitle>Nat Commun</stitle><addtitle>Nat Commun</addtitle><date>2019-04-16</date><risdate>2019</risdate><volume>10</volume><issue>1</issue><spage>1774</spage><epage>1774</epage><pages>1774-1774</pages><artnum>1774</artnum><issn>2041-1723</issn><eissn>2041-1723</eissn><abstract>Toluene and its derivatives are petroleum-derived raw materials produced from gasoline by catalytic reformation. These abundant chemical feedstocks are commonly used as solvents in organic synthesis. The C(sp
3
)−H functionalization of these unactivated substrates has been widely used to directly introduce benzylic motifs into diverse molecules to furnish important compounds. Despite these advances, progress in asymmetric catalysis remains underdeveloped. Here, we report photoinduced radical-based enantioselective C(sp
3
)−C(sp
3
) coupling reactions of activated ketones with toluene and its derivatives by means of chiral acid catalysis. With a La(OTf)
3
/pybox complex catalyst, a variety of chiral 3-hydroxy-3-benzyl-substituted 2-oxindoles, including many conventionally difficult-to-access variants, are obtained directly from isatins in high yields with good to excellent enantioselectivities. Acenaphthoquinone is also compatible with the use of a chiral phosphoric acid (CPA) catalyst, leading to another series of important enantioenriched tertiary alcohols.
Asymmetric transformations involving abundant chemical feedstocks such as toluene and its derivatives are rather rare. Here, the authors report the radical enantioselective C(sp
3
) −C(sp
3
) coupling of activated ketones with toluenes by means of chiral acid catalysis to afford enantioenriched tertiary alcohols.</abstract><cop>London</cop><pub>Nature Publishing Group UK</pub><pmid>30992448</pmid><doi>10.1038/s41467-019-09857-9</doi><tpages>1</tpages><orcidid>https://orcid.org/0000-0002-6350-7429</orcidid><orcidid>https://orcid.org/0000-0003-1264-4914</orcidid><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
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| ispartof | Nature communications, 2019-04, Vol.10 (1), p.1774-1774, Article 1774 |
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| language | eng |
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| source | Publicly Available Content Database; Nature; PubMed Central; Springer Nature - nature.com Journals - Fully Open Access |
| subjects | 119/118 140/131 140/146 140/58 639/638/439/890 639/638/77/883 639/638/77/888 Alcohols Catalysis Catalysts Chemical reactions Coupling (molecular) Derivatives Enantiomers Gasoline Humanities and Social Sciences Ketones multidisciplinary Organic chemistry Phosphoric acid Raw materials Science Science (multidisciplinary) Substrates Toluene |
| title | Chiral acid-catalysed enantioselective C−H functionalization of toluene and its derivatives driven by visible light |
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