Suzuki–Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs
The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-...
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| Published in | Journal of organic chemistry Vol. 77; no. 22; pp. 10399 - 10408 |
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| Main Authors | , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society
16.11.2012
Amer Chemical Soc |
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| Abstract | The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides. |
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| AbstractList | The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides. |
| Author | Presset, Marc Rombouts, Frederik Molander, Gary A Colombel, Virginie Oehlrich, Daniel Fleury-Brégeot, Nicolas Beaumard, Floriane |
| AuthorAffiliation | Janssen Pharmaceutica University of Pennsylvania |
| AuthorAffiliation_xml | – name: University of Pennsylvania – name: Janssen Pharmaceutica |
| Author_xml | – sequence: 1 givenname: Nicolas surname: Fleury-Brégeot fullname: Fleury-Brégeot, Nicolas – sequence: 2 givenname: Marc surname: Presset fullname: Presset, Marc – sequence: 3 givenname: Floriane surname: Beaumard fullname: Beaumard, Floriane – sequence: 4 givenname: Virginie surname: Colombel fullname: Colombel, Virginie – sequence: 5 givenname: Daniel surname: Oehlrich fullname: Oehlrich, Daniel – sequence: 6 givenname: Frederik surname: Rombouts fullname: Rombouts, Frederik email: gmolandr@sas.upenn.edu, FROMBOUT@its.jnj.com – sequence: 7 givenname: Gary A surname: Molander fullname: Molander, Gary A email: gmolandr@sas.upenn.edu, FROMBOUT@its.jnj.com |
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| Keywords | BOC-PROTECTED AMINOMETHYLTRIFLUOROBORATE BORONIC ACID HYDROBORATION ETHERS ARYL CATALYZED BORYLATION ALKYLBORONIC ESTERS DERIVATIVES C-H BONDS ALKYL-HALIDES Suzuki coupling Potassium compound Cross reaction Organic bromine compounds Aromatic compound Chemical synthesis Potassium Heterocyclic compound |
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| Snippet | The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons... |
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| SubjectTerms | B derivatives Borates - chemistry Catalysis Chemistry Chemistry, Organic Exact sciences and technology Heterocyclic compounds Heterocyclic Compounds - chemical synthesis Heterocyclic Compounds - chemistry Molecular Structure Organic chemistry Organometalloidal and organometallic compounds Oxygen - chemistry Physical Sciences Potassium - chemistry Preparations and properties Science & Technology |
| Title | Suzuki–Miyaura Cross-Coupling of Potassium Alkoxyethyltrifluoroborates: Access to Aryl/Heteroarylethyloxy Motifs |
| URI | http://dx.doi.org/10.1021/jo3021665 http://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcApp=Summon&SrcAuth=ProQuest&DestApp=WOS&DestLinkType=FullRecord&UT=000311073000048 https://www.ncbi.nlm.nih.gov/pubmed/23131122 https://search.proquest.com/docview/1171867196 |
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