Photocatalytic Dehydrogenative Cross‐Coupling of Alkenes with Alcohols or Azoles without External Oxidant
Direct cross‐coupling between alkenes/R‐H or alkenes/RXH is a dream reaction, especially without external oxidants. Inputting energy by photocatalysis and employing a cobalt catalyst as a two‐electron acceptor, a direct C−H/X−H cross‐coupling with H2 evolution has been achieved for C−O and C−N bond...
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| Veröffentlicht in: | Angewandte Chemie International Edition 2017-01, Vol.56 (4), p.1120-1124 |
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| container_title | Angewandte Chemie International Edition |
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| creator | Yi, Hong Niu, Linbin Song, Chunlan Li, Yiying Dou, Bowen Singh, Atul K. Lei, Aiwen |
| description | Direct cross‐coupling between alkenes/R‐H or alkenes/RXH is a dream reaction, especially without external oxidants. Inputting energy by photocatalysis and employing a cobalt catalyst as a two‐electron acceptor, a direct C−H/X−H cross‐coupling with H2 evolution has been achieved for C−O and C−N bond formation. A new radical alkenylation using alkene as the redox compound is presented. A wide range of aliphatic alcohols—even long chain alcohols—are tolerated well in this system, providing a new route to multi‐substituted enol ether derivatives using simple alkenes. Additionally, this protocol can also be used for N‐vinylazole synthesis. Mechanistic insights reveal that the cobalt catalyst oxidizes the photocatalyst to revive the photocatalytic cycle.
Footloose and oxidant‐free: A photocatalytic process that employs a cobalt catalyst as an electron acceptor mediates direct C−H/X−H cross‐coupling and H2 evolution, achieving C−O and C−N bond formation. |
| doi_str_mv | 10.1002/anie.201609274 |
| format | Article |
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Footloose and oxidant‐free: A photocatalytic process that employs a cobalt catalyst as an electron acceptor mediates direct C−H/X−H cross‐coupling and H2 evolution, achieving C−O and C−N bond formation.</description><subject>Alcohol</subject><subject>Alcohols</subject><subject>Aliphatic alcohols</subject><subject>Aliphatic compounds</subject><subject>Alkenes</subject><subject>Antifungal agents</subject><subject>Azoles</subject><subject>Catalysis</subject><subject>Catalysts</subject><subject>Chemical synthesis</subject><subject>Cobalt</subject><subject>Coupling</subject><subject>C−N bond formation</subject><subject>C−O bond formation</subject><subject>Dehydrogenation</subject><subject>Heterocyclic compounds</subject><subject>oxidant-free</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><subject>Photocatalysis</subject><subject>radical alkenylation</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFkcFOGzEURS3UCmhgy7Ky1A2bSZ_t8dizjNLQIiHooqwtx-MQgzNOx55CWPEJfCNfUkcJQeqCrvxsnXdk3YvQCYEhAaBfdevskAKpoKai3EOHhFNSMCHYhzyXjBVCcnKAPsV4m3kpodpHB1TUNQhaHaK7n_OQgtFJ-1VyBn-z81XThRvb6uT-WDzuQowvT8_j0C-9a29wmOGRv7OtjfjepXm-mDAPPuLQ4dFj8Nv30Cc8eUi2a7XHVw-u0W06Qh9n2kd7vD0H6Pps8mv8o7i4-n4-Hl0UpmSyLDhUFDiAIdQ2s6rRRpOS1hIkB1FDYxilhGhZasZ4xQiZVnzaUC6mhktKNRug04132YXfvY1JLVw01nvd2tBHRXIiOYlSsIx--Qe9Df36z1FRyBkRKUC8R2WXBADOy0wNN5RZZ9bZmVp2bqG7lSKg1mWpdVlqV1Ze-LzV9tOFbXb4azsZqDfAvfN29R-dGl2eT97kfwEojqBP</recordid><startdate>20170119</startdate><enddate>20170119</enddate><creator>Yi, Hong</creator><creator>Niu, Linbin</creator><creator>Song, Chunlan</creator><creator>Li, Yiying</creator><creator>Dou, Bowen</creator><creator>Singh, Atul K.</creator><creator>Lei, Aiwen</creator><general>Wiley Subscription Services, Inc</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7TM</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-8417-3061</orcidid></search><sort><creationdate>20170119</creationdate><title>Photocatalytic Dehydrogenative Cross‐Coupling of Alkenes with Alcohols or Azoles without External Oxidant</title><author>Yi, Hong ; Niu, Linbin ; Song, Chunlan ; Li, Yiying ; Dou, Bowen ; Singh, Atul K. ; Lei, Aiwen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4384-50620500c12edf6daca142980850790dc32211a84a3356311b65bd257bc5822a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>Alcohol</topic><topic>Alcohols</topic><topic>Aliphatic alcohols</topic><topic>Aliphatic compounds</topic><topic>Alkenes</topic><topic>Antifungal agents</topic><topic>Azoles</topic><topic>Catalysis</topic><topic>Catalysts</topic><topic>Chemical synthesis</topic><topic>Cobalt</topic><topic>Coupling</topic><topic>C−N bond formation</topic><topic>C−O bond formation</topic><topic>Dehydrogenation</topic><topic>Heterocyclic compounds</topic><topic>oxidant-free</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><topic>Photocatalysis</topic><topic>radical alkenylation</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yi, Hong</creatorcontrib><creatorcontrib>Niu, Linbin</creatorcontrib><creatorcontrib>Song, Chunlan</creatorcontrib><creatorcontrib>Li, Yiying</creatorcontrib><creatorcontrib>Dou, Bowen</creatorcontrib><creatorcontrib>Singh, Atul K.</creatorcontrib><creatorcontrib>Lei, Aiwen</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><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>Yi, Hong</au><au>Niu, Linbin</au><au>Song, Chunlan</au><au>Li, Yiying</au><au>Dou, Bowen</au><au>Singh, Atul K.</au><au>Lei, Aiwen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Photocatalytic Dehydrogenative Cross‐Coupling of Alkenes with Alcohols or Azoles without External Oxidant</atitle><jtitle>Angewandte Chemie International Edition</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2017-01-19</date><risdate>2017</risdate><volume>56</volume><issue>4</issue><spage>1120</spage><epage>1124</epage><pages>1120-1124</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><coden>ACIEAY</coden><abstract>Direct cross‐coupling between alkenes/R‐H or alkenes/RXH is a dream reaction, especially without external oxidants. Inputting energy by photocatalysis and employing a cobalt catalyst as a two‐electron acceptor, a direct C−H/X−H cross‐coupling with H2 evolution has been achieved for C−O and C−N bond formation. A new radical alkenylation using alkene as the redox compound is presented. A wide range of aliphatic alcohols—even long chain alcohols—are tolerated well in this system, providing a new route to multi‐substituted enol ether derivatives using simple alkenes. Additionally, this protocol can also be used for N‐vinylazole synthesis. Mechanistic insights reveal that the cobalt catalyst oxidizes the photocatalyst to revive the photocatalytic cycle.
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alcohol Alcohols Aliphatic alcohols Aliphatic compounds Alkenes Antifungal agents Azoles Catalysis Catalysts Chemical synthesis Cobalt Coupling C−N bond formation C−O bond formation Dehydrogenation Heterocyclic compounds oxidant-free Oxidants Oxidizing agents Photocatalysis radical alkenylation |
| title | Photocatalytic Dehydrogenative Cross‐Coupling of Alkenes with Alcohols or Azoles without External Oxidant |
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