Vitamin B12‐Photocatalyzed Cyclopropanation of Electron‐Deficient Alkenes Using Dichloromethane as the Methylene Source
The cyclopropyl group is of great importance in medicinal chemistry, as it can be leveraged to influence a range of pharmaceutical properties in drug molecules. This report describes a Vitamin B12‐photocatalyzed approach for the cyclopropanation of electron‐deficient alkenes using dichloromethane (C...
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Veröffentlicht in: | Angewandte Chemie International Edition 2024-01, Vol.63 (2), p.e202316064-n/a |
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description | The cyclopropyl group is of great importance in medicinal chemistry, as it can be leveraged to influence a range of pharmaceutical properties in drug molecules. This report describes a Vitamin B12‐photocatalyzed approach for the cyclopropanation of electron‐deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction proceeds in good to excellent yields under mild conditions, has excellent functional group compatibility, and is highly chemoselective. The scope could also be extended to the preparation of D2‐cyclopropyl and methyl‐substituted cyclopropyl adducts starting from CD2Cl2 and 1,1‐dichloroethane, respectively.
We report a vitamin B12‐photocatalyzed strategy for the cyclopropanation of electron‐deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction has excellent functional group tolerance, is highly chemoselective, and the scope can be extended to other 1,1‐dichloroalkanes for the preparation of D2‐cyclopropyl and methyl‐substituted cyclopropyl adducts, all of which are important isosteres in medical chemistry. |
doi_str_mv | 10.1002/anie.202316064 |
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We report a vitamin B12‐photocatalyzed strategy for the cyclopropanation of electron‐deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction has excellent functional group tolerance, is highly chemoselective, and the scope can be extended to other 1,1‐dichloroalkanes for the preparation of D2‐cyclopropyl and methyl‐substituted cyclopropyl adducts, all of which are important isosteres in medical chemistry.</description><edition>International ed. in English</edition><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.202316064</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Adducts ; Alkenes ; Cobalt ; Cyanocobalamin ; Cyclopropanation ; Dichloroethane ; Dichloromethane ; Functional groups ; Organic compounds ; Photocatalysis ; Radicals ; Visible Light ; Vitamin B12</subject><ispartof>Angewandte Chemie International Edition, 2024-01, Vol.63 (2), p.e202316064-n/a</ispartof><rights>2023 Wiley‐VCH GmbH</rights><rights>2024 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-7954-5403 ; 0009-0000-3989-7503 ; 0000-0001-6161-7133</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.202316064$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.202316064$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Teye‐Kau, John Hayford G.</creatorcontrib><creatorcontrib>Ayodele, Mayokun J.</creatorcontrib><creatorcontrib>Pitre, Spencer P.</creatorcontrib><title>Vitamin B12‐Photocatalyzed Cyclopropanation of Electron‐Deficient Alkenes Using Dichloromethane as the Methylene Source</title><title>Angewandte Chemie International Edition</title><description>The cyclopropyl group is of great importance in medicinal chemistry, as it can be leveraged to influence a range of pharmaceutical properties in drug molecules. This report describes a Vitamin B12‐photocatalyzed approach for the cyclopropanation of electron‐deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction proceeds in good to excellent yields under mild conditions, has excellent functional group compatibility, and is highly chemoselective. The scope could also be extended to the preparation of D2‐cyclopropyl and methyl‐substituted cyclopropyl adducts starting from CD2Cl2 and 1,1‐dichloroethane, respectively.
We report a vitamin B12‐photocatalyzed strategy for the cyclopropanation of electron‐deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction has excellent functional group tolerance, is highly chemoselective, and the scope can be extended to other 1,1‐dichloroalkanes for the preparation of D2‐cyclopropyl and methyl‐substituted cyclopropyl adducts, all of which are important isosteres in medical chemistry.</description><subject>Adducts</subject><subject>Alkenes</subject><subject>Cobalt</subject><subject>Cyanocobalamin</subject><subject>Cyclopropanation</subject><subject>Dichloroethane</subject><subject>Dichloromethane</subject><subject>Functional groups</subject><subject>Organic compounds</subject><subject>Photocatalysis</subject><subject>Radicals</subject><subject>Visible Light</subject><subject>Vitamin B12</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNpdkcFOGzEQhlcVlQq0154tceGyYI93vetjSAJESgsSTa-W2YyJwbHD2lG15cIj9Bn7JDVKlQOH0cwvfRr9M39RfGX0jFEK59pbPAMKnAkqqg_FIauBlbxp-EGeK87Lpq3Zp-IoxsfMty0Vh8XLT5v02npyweDv65_bVUih00m74TcuyXjoXNj0YaO9TjZ4EgyZOuxSH3ymJ2hsZ9EnMnJP6DGSRbT-gUxst3KhD2tMK-2R6EjSCsm3LAeXOXIXtn2Hn4uPRruIX_7342JxOf0xvi7nN1ez8WhebkCIqpS8qgBbkMCkMYwJg-1S6ha1YRKMaIQRuIRcmjFcYkM75LoSTNc1cLjnx8Xpbm--5HmLMam1jR06l72FbVTQyhoEqwXN6Mk79DFb9dmdApm_zLmUkCm5o35Zh4Pa9Hat-0Exqt6CUG9BqH0QavR9Nt0r_g-fwIIP</recordid><startdate>20240108</startdate><enddate>20240108</enddate><creator>Teye‐Kau, John Hayford G.</creator><creator>Ayodele, Mayokun J.</creator><creator>Pitre, Spencer P.</creator><general>Wiley Subscription Services, Inc</general><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7954-5403</orcidid><orcidid>https://orcid.org/0009-0000-3989-7503</orcidid><orcidid>https://orcid.org/0000-0001-6161-7133</orcidid></search><sort><creationdate>20240108</creationdate><title>Vitamin B12‐Photocatalyzed Cyclopropanation of Electron‐Deficient Alkenes Using Dichloromethane as the Methylene Source</title><author>Teye‐Kau, John Hayford G. ; Ayodele, Mayokun J. ; Pitre, Spencer P.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p2664-93442e829219ff116fe8d9a8eaf192f676f6ed26eda11ede70ce3a461a55232b3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Adducts</topic><topic>Alkenes</topic><topic>Cobalt</topic><topic>Cyanocobalamin</topic><topic>Cyclopropanation</topic><topic>Dichloroethane</topic><topic>Dichloromethane</topic><topic>Functional groups</topic><topic>Organic compounds</topic><topic>Photocatalysis</topic><topic>Radicals</topic><topic>Visible Light</topic><topic>Vitamin B12</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Teye‐Kau, John Hayford G.</creatorcontrib><creatorcontrib>Ayodele, Mayokun J.</creatorcontrib><creatorcontrib>Pitre, Spencer P.</creatorcontrib><collection>Nucleic Acids Abstracts</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie International Edition</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Teye‐Kau, John Hayford G.</au><au>Ayodele, Mayokun J.</au><au>Pitre, Spencer P.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Vitamin B12‐Photocatalyzed Cyclopropanation of Electron‐Deficient Alkenes Using Dichloromethane as the Methylene Source</atitle><jtitle>Angewandte Chemie International Edition</jtitle><date>2024-01-08</date><risdate>2024</risdate><volume>63</volume><issue>2</issue><spage>e202316064</spage><epage>n/a</epage><pages>e202316064-n/a</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>The cyclopropyl group is of great importance in medicinal chemistry, as it can be leveraged to influence a range of pharmaceutical properties in drug molecules. This report describes a Vitamin B12‐photocatalyzed approach for the cyclopropanation of electron‐deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction proceeds in good to excellent yields under mild conditions, has excellent functional group compatibility, and is highly chemoselective. The scope could also be extended to the preparation of D2‐cyclopropyl and methyl‐substituted cyclopropyl adducts starting from CD2Cl2 and 1,1‐dichloroethane, respectively.
We report a vitamin B12‐photocatalyzed strategy for the cyclopropanation of electron‐deficient alkenes using dichloromethane (CH2Cl2) as the methylene source. The reaction has excellent functional group tolerance, is highly chemoselective, and the scope can be extended to other 1,1‐dichloroalkanes for the preparation of D2‐cyclopropyl and methyl‐substituted cyclopropyl adducts, all of which are important isosteres in medical chemistry.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/anie.202316064</doi><tpages>6</tpages><edition>International ed. in English</edition><orcidid>https://orcid.org/0000-0002-7954-5403</orcidid><orcidid>https://orcid.org/0009-0000-3989-7503</orcidid><orcidid>https://orcid.org/0000-0001-6161-7133</orcidid></addata></record> |
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subjects | Adducts Alkenes Cobalt Cyanocobalamin Cyclopropanation Dichloroethane Dichloromethane Functional groups Organic compounds Photocatalysis Radicals Visible Light Vitamin B12 |
title | Vitamin B12‐Photocatalyzed Cyclopropanation of Electron‐Deficient Alkenes Using Dichloromethane as the Methylene Source |
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