Enantioselective and Regioselective Copper-Catalyzed Borocyanation of 1-Aryl-1,3-Butadienes
journal contribution
posted on 2019-07-01, 10:13 authored by T Jia, MJ Smith, A Pulis, GJP Perry, DJ ProcterA multicomponent copper-catalyzed enantio- and regioselective borocyanation of 1-aryl-1,3-butadienes has been developed. The method provides access to functionalized allylic nitriles in up to 90% yield and 94% ee and thus overcomes some of the long-standing problems associated with the enantioselective insertion of cyano groups into unsaturated organic molecules. Both boron and cyano functionalities can be used as handles for selective manipulation.
Funding
We thank the EPSRC (Established Career Fellowship to D.J.P.; EP/M005062/1), the Royal Society (Newton International Fellowship to T.J.), and the University of Manchester (Lectureships to A.P.P. and G.J.P.P). We also thank the X-ray Crystallography Service at the University of Manchester.
History
Citation
ACS Catalysis, 2019, 9, pp. 4744-6750Author affiliation
/Organisation/COLLEGE OF SCIENCE AND ENGINEERING/Department of ChemistryVersion
- AM (Accepted Manuscript)
Published in
ACS CatalysisPublisher
American Chemical Societyissn
2155-5435Copyright date
2019Publisher DOI
Publisher version
https://pubs.acs.org/doi/10.1021/acscatal.9b01911Notes
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscatal.9b01911. Experimental procedures and characterization data (PDF) Crystallographic file (CIF) Crystallographic file (CIF) Crystallographic file (CIF);The file associated with this record is under embargo until 12 months after publication, in accordance with the publisher's self-archiving policy. The full text may be available through the publisher links provided above.Language
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