Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst
The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source....
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| Published in | Organic letters Vol. 22; no. 10; pp. 3765 - 3769 |
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| Main Authors | , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
15.05.2020
Amer Chemical Soc |
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| Abstract | The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions. |
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| AbstractList | The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions. The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions. The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is achieved by applying 2 mol % of a manganese precatalyst based on the readily accessible bis(imino)pyridine ligand and MnCl2 as metal source. Propargylic alcohols and amines, as well as symmetric internal alkynes, were efficiently converted into the corresponding functionalized alkenes, which can serve as important and valuable intermediates for further synthetic applications such as cross-coupling reactions. |
| Author | Rueping, Magnus Ganardi, Ruth-Christine Brzozowska, Aleksandra Zubar, Viktoriia |
| AuthorAffiliation | King Abdullah University of Science and Technology (KAUST) KAUST Catalysis Center (KCC) Institute of Organic Chemistry |
| AuthorAffiliation_xml | – name: KAUST Catalysis Center (KCC) – name: King Abdullah University of Science and Technology (KAUST) – name: Institute of Organic Chemistry |
| Author_xml | – sequence: 1 givenname: Aleksandra surname: Brzozowska fullname: Brzozowska, Aleksandra organization: Institute of Organic Chemistry – sequence: 2 givenname: Viktoriia surname: Zubar fullname: Zubar, Viktoriia organization: Institute of Organic Chemistry – sequence: 3 givenname: Ruth-Christine surname: Ganardi fullname: Ganardi, Ruth-Christine organization: Institute of Organic Chemistry – sequence: 4 givenname: Magnus orcidid: 0000-0003-4580-5227 surname: Rueping fullname: Rueping, Magnus email: magnus.rueping@rwth-aachen.de organization: King Abdullah University of Science and Technology (KAUST) |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/32227972$$D View this record in MEDLINE/PubMed |
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| Snippet | The first manganese-catalyzed hydroboration of propargylic alcohols and amines as well as internal alkynes is reported. High regio- and stereoselectivity is... |
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| SubjectTerms | Chemistry Chemistry, Organic Physical Sciences Science & Technology |
| Title | Chemoselective Hydroboration of Propargylic Alcohols and Amines Using a Manganese(II) Catalyst |
| URI | http://dx.doi.org/10.1021/acs.orglett.0c00941 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000535292300006 https://www.ncbi.nlm.nih.gov/pubmed/32227972 https://search.proquest.com/docview/2385276128 |
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