Atroposelective Sulfenylation of Biaryl Anilines Catalyzed by Chiral SPINOL-Derived Selenide
The atroposelective electrophilic sulfenylation of biaryl anilines has been realized for the first time. The reaction is enabled by a new chiral 6,6′-dianisole substituted SPINOL-derived selenide. A variety of axially chiral sulfur-containing biaryl aniline compounds were obtained in moderate to exc...
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Veröffentlicht in: | Organic letters 2023-05, Vol.25 (19), p.3445-3450 |
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creator | Zhang, Xin-Yu Zhu, Deng Huo, Yu-Xuan Chen, Ling-Ling Chen, Zhi-Min |
description | The atroposelective electrophilic sulfenylation of biaryl anilines has been realized for the first time. The reaction is enabled by a new chiral 6,6′-dianisole substituted SPINOL-derived selenide. A variety of axially chiral sulfur-containing biaryl aniline compounds were obtained in moderate to excellent yields with moderate to excellent enantioselectivities. The experimental results suggest that catalyst rigidity is important for the high atroposelectivity. |
doi_str_mv | 10.1021/acs.orglett.3c01002 |
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The reaction is enabled by a new chiral 6,6′-dianisole substituted SPINOL-derived selenide. A variety of axially chiral sulfur-containing biaryl aniline compounds were obtained in moderate to excellent yields with moderate to excellent enantioselectivities. 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Lett</addtitle><description>The atroposelective electrophilic sulfenylation of biaryl anilines has been realized for the first time. The reaction is enabled by a new chiral 6,6′-dianisole substituted SPINOL-derived selenide. A variety of axially chiral sulfur-containing biaryl aniline compounds were obtained in moderate to excellent yields with moderate to excellent enantioselectivities. 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Lett</addtitle><date>2023-05-19</date><risdate>2023</risdate><volume>25</volume><issue>19</issue><spage>3445</spage><epage>3450</epage><pages>3445-3450</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The atroposelective electrophilic sulfenylation of biaryl anilines has been realized for the first time. The reaction is enabled by a new chiral 6,6′-dianisole substituted SPINOL-derived selenide. A variety of axially chiral sulfur-containing biaryl aniline compounds were obtained in moderate to excellent yields with moderate to excellent enantioselectivities. The experimental results suggest that catalyst rigidity is important for the high atroposelectivity.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>37166143</pmid><doi>10.1021/acs.orglett.3c01002</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-6988-8955</orcidid></addata></record> |
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title | Atroposelective Sulfenylation of Biaryl Anilines Catalyzed by Chiral SPINOL-Derived Selenide |
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