A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C–H Alkylation of Alcohols
Abstract The development of catalyst-controlled, site-selective C(sp 3 )–H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An elec...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2020-08, Vol.52 (15), p.2171-2189 |
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| container_title | Synthesis (Stuttgart) |
| container_volume | 52 |
| creator | Sakai, Kentaro Oisaki, Kounosuke Kanai, Motomu |
| description | Abstract
The development of catalyst-controlled, site-selective C(sp
3
)–H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid–ethanolamine complex enhances the chemical yield of the α-C–H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched peptides. |
| doi_str_mv | 10.1055/s-0040-1707114 |
| format | Article |
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The development of catalyst-controlled, site-selective C(sp
3
)–H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid–ethanolamine complex enhances the chemical yield of the α-C–H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched peptides.</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0040-1707114</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><subject>Chemistry ; Chemistry, Organic ; feature ; Physical Sciences ; Science & Technology</subject><ispartof>Synthesis (Stuttgart), 2020-08, Vol.52 (15), p.2171-2189</ispartof><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>true</woscitedreferencessubscribed><woscitedreferencescount>22</woscitedreferencescount><woscitedreferencesoriginalsourcerecordid>wos000550218500004</woscitedreferencesoriginalsourcerecordid><citedby>FETCH-LOGICAL-c317t-62de860f6c11c79619b6d8ecb3872156c06f4d97206c5a5d9e506c46cb30bae93</citedby><cites>FETCH-LOGICAL-c317t-62de860f6c11c79619b6d8ecb3872156c06f4d97206c5a5d9e506c46cb30bae93</cites><orcidid>0000-0003-1977-7648 ; 0000-0002-0499-8168</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0040-1707114.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0040-1707114$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>315,782,786,3019,3020,27931,27932,28255,54566,54567</link.rule.ids></links><search><creatorcontrib>Sakai, Kentaro</creatorcontrib><creatorcontrib>Oisaki, Kounosuke</creatorcontrib><creatorcontrib>Kanai, Motomu</creatorcontrib><title>A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C–H Alkylation of Alcohols</title><title>Synthesis (Stuttgart)</title><addtitle>SYNTHESIS-STUTTGART</addtitle><addtitle>Synthesis</addtitle><description>Abstract
The development of catalyst-controlled, site-selective C(sp
3
)–H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid–ethanolamine complex enhances the chemical yield of the α-C–H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched peptides.</description><subject>Chemistry</subject><subject>Chemistry, Organic</subject><subject>feature</subject><subject>Physical Sciences</subject><subject>Science & Technology</subject><issn>0039-7881</issn><issn>1437-210X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid>AOWDO</sourceid><recordid>eNqNkE1OwzAQRi0EEqWwZZ09chknsZ0sSwS0UiWQAMEucp0JTZvGVewC3XEHTsJFOAQnwf0ROyRWnk_63sjzCDll0GPA-bmlADFQJkEyFu-RDosjSUMGT_ukAxClVCYJOyRH1k4BQIZR2iF1P7gwTUEfUc2wqZpnH9uqUQ6DTDlVr6wL3ES5YDhftOYFrU8Y3GmzwMCUm3A7Mc60WJi34OuTZt_vH4OgX89WtXKVadatfq3NxNT2mByUqrZ4snu75OHq8j4b0NHN9TDrj6iOmHRUhAUmAkqhGdMyFSwdiyJBPY4SGTIuNIgyLlIZgtBc8SJF7qdY-AKMFaZRl_S2e3VrrG2xzBdtNVftKmeQr13lNl-7yneuPJBsgVccm9LqChuNv5CXxTmELOF-gjir3OayzCwb59Gz_6O-TbdtN6lwjvnULNvGq_jrYz_tZYyq</recordid><startdate>20200804</startdate><enddate>20200804</enddate><creator>Sakai, Kentaro</creator><creator>Oisaki, Kounosuke</creator><creator>Kanai, Motomu</creator><general>Georg Thieme Verlag</general><general>Thieme Medical Publishers</general><scope>1KM</scope><scope>AOWDO</scope><scope>BLEPL</scope><scope>DTL</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0003-1977-7648</orcidid><orcidid>https://orcid.org/0000-0002-0499-8168</orcidid></search><sort><creationdate>20200804</creationdate><title>A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C–H Alkylation of Alcohols</title><author>Sakai, Kentaro ; Oisaki, Kounosuke ; Kanai, Motomu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c317t-62de860f6c11c79619b6d8ecb3872156c06f4d97206c5a5d9e506c46cb30bae93</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Chemistry</topic><topic>Chemistry, Organic</topic><topic>feature</topic><topic>Physical Sciences</topic><topic>Science & Technology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Sakai, Kentaro</creatorcontrib><creatorcontrib>Oisaki, Kounosuke</creatorcontrib><creatorcontrib>Kanai, Motomu</creatorcontrib><collection>Index Chemicus</collection><collection>Web of Science - Science Citation Index Expanded - 2020</collection><collection>Web of Science Core Collection</collection><collection>Science Citation Index Expanded</collection><collection>CrossRef</collection><jtitle>Synthesis (Stuttgart)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Sakai, Kentaro</au><au>Oisaki, Kounosuke</au><au>Kanai, Motomu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C–H Alkylation of Alcohols</atitle><jtitle>Synthesis (Stuttgart)</jtitle><stitle>SYNTHESIS-STUTTGART</stitle><addtitle>Synthesis</addtitle><date>2020-08-04</date><risdate>2020</risdate><volume>52</volume><issue>15</issue><spage>2171</spage><epage>2189</epage><pages>2171-2189</pages><issn>0039-7881</issn><eissn>1437-210X</eissn><abstract>Abstract
The development of catalyst-controlled, site-selective C(sp
3
)–H functionalization reactions is currently a major challenge in organic synthesis. In this paper, a novel bond-weakening catalyst that recognizes the hydroxy group of alcohols through formation of a borate is described. An electron-deficient borinic acid–ethanolamine complex enhances the chemical yield of the α-C–H alkylation of alcohols when used in conjunction with a photoredox catalyst and a hydrogen atom transfer catalyst under irradiation with visible light. This ternary hybrid catalyst system can, for example, be applied to functional-group-enriched peptides.</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0040-1707114</doi><tpages>19</tpages><orcidid>https://orcid.org/0000-0003-1977-7648</orcidid><orcidid>https://orcid.org/0000-0002-0499-8168</orcidid><oa>free_for_read</oa></addata></record> |
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| ispartof | Synthesis (Stuttgart), 2020-08, Vol.52 (15), p.2171-2189 |
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| source | Web of Science - Science Citation Index Expanded - 2020<img src="https://exlibris-pub.s3.amazonaws.com/fromwos-v2.jpg" />; Thieme Connect Journals |
| subjects | Chemistry Chemistry, Organic feature Physical Sciences Science & Technology |
| title | A Bond-Weakening Borinate Catalyst that Improves the Scope of the Photoredox α-C–H Alkylation of Alcohols |
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