Suzuki-Miyaura homocoupling of naphthyl triflates using bis(pinacolato)diboron: approaches to the biaryl skeleton of crisamicin A

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dc.contributor.author Brimble, MA en
dc.contributor.author Lai, MYH en
dc.date.accessioned 2011-09-19T21:13:00Z en
dc.date.issued 2003 en
dc.identifier.citation Organic & Biomolecular Chemistry 1(12):2084-2095 2003 en
dc.identifier.issn 1477-0520 en
dc.identifier.uri http://hdl.handle.net/2292/8128 en
dc.description.abstract Homocoupling of naphthyl triflates 27, 16, 17 to the respective binaphthyls 28, 31 and 35 has been achieved in a one-pot procedure using bis(pinacolato)diboron and PdCl2(dppf). Use of potassium acetate as the base provides access to the initial naphthylboronate intermediates whereas the stronger base potassium phosphate is required in order to promote subsequent coupling of the naphthylboronate with a second equivalent of the naphthyl triflate. Attempts to convert binaphthyl 35 into bis-acetylnaphthalene 14, a key intermediate for the synthesis of the dimeric pyranonaphthoquinone antibiotic crisamicin A 2, via double Fries rearrangement of bis-acetate 37 derived from binaphthyl 35, were unsuccessful. Attempts to introduce the acetyl groups at C-7 and C-7′ on bis-acetylnaphthalene 14via Fries rearrangement of the monomeric precursors 21 and 15, before effecting homocoupling to a biaryl were unsuccessful. Introduction of an acetyl group via initial bromination ortho to the hydroxyl group in naphthol 18, which bears an electron rich benzyl ether at C-7, was plagued by the formation of phenolic coupling product 42 and naphthoquinone 43. Bromination of naphthol 45, bearing a less electron rich triflate group at C-7, also afforded binaphthol 47 resulting from phenolic coupling as well as naphthoquinone 48 when using N-bromosuccinimide at low temperature. en
dc.language EN en
dc.relation.ispartofseries Organic & Biomolecular Chemistry en
dc.rights Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. Details obtained from http://www.sherpa.ac.uk/romeo/issn/1477-0520/ en
dc.rights.uri https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm en
dc.subject PYRANONAPHTHOQUINONE ANTIBIOTICS en
dc.subject COUPLING REACTION en
dc.subject SYNTHETIC ROUTE en
dc.subject ARYL HALIDES en
dc.subject MICROMONOSPORA en
dc.subject DIALKOXYBORANE en
dc.title Suzuki-Miyaura homocoupling of naphthyl triflates using bis(pinacolato)diboron: approaches to the biaryl skeleton of crisamicin A en
dc.type Journal Article en
dc.identifier.doi 10.1039/b303070a en
pubs.issue 12 en
pubs.begin-page 2084 en
pubs.volume 1 en
dc.rights.holder Copyright: 2003 Royal Society of Chemistry en
dc.identifier.pmid 12945899 en
pubs.end-page 2095 en
dc.rights.accessrights http://purl.org/eprint/accessRights/RestrictedAccess en
pubs.subtype Article en
pubs.elements-id 6024 en
pubs.org-id Science en
pubs.org-id Chemistry en
pubs.org-id Science Research en
pubs.org-id Maurice Wilkins Centre (2010-2014) en
pubs.record-created-at-source-date 2010-09-01 en
pubs.dimensions-id 12945899 en


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