One-pot homologation of boronic acids: a platform for diversity-oriented synthesis

Calum W. Muir, Julien C. Vantourout, Albert Isidro-Llobet, Simon J. F. Macdonald, Allan J. B. Watson

Research output: Contribution to journalArticle

16 Citations (Scopus)

Abstract

Formal homologation of sp2-hybridized boronic acids is achieved via cross-coupling of boronic acids with conjunctive haloaryl BMIDA components in the presence of a suitably balanced basic phase. The utility of this approach to provide a platform for diversity-oriented synthesis in discovery medicinal chemistry is demonstrated in the context of the synthesis of a series of analogues of a BET bromodomain inhibitor.
LanguageEnglish
Pages6030–6033
Number of pages4
JournalOrganic Letters
Volume17
Issue number24
DOIs
Publication statusPublished - 3 Dec 2015

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Boronic Acids
platforms
acids
Pharmaceutical Chemistry
cross coupling
synthesis
inhibitors
chemistry
analogs

Keywords

  • boronic acids
  • chemical reactivity
  • organometallic reagents

Cite this

Muir, C. W., Vantourout, J. C., Isidro-Llobet, A., Macdonald, S. J. F., & Watson, A. J. B. (2015). One-pot homologation of boronic acids: a platform for diversity-oriented synthesis. Organic Letters, 17(24), 6030–6033. https://doi.org/10.1021/acs.orglett.5b03030
Muir, Calum W. ; Vantourout, Julien C. ; Isidro-Llobet, Albert ; Macdonald, Simon J. F. ; Watson, Allan J. B. / One-pot homologation of boronic acids : a platform for diversity-oriented synthesis. In: Organic Letters. 2015 ; Vol. 17, No. 24. pp. 6030–6033.
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Muir, CW, Vantourout, JC, Isidro-Llobet, A, Macdonald, SJF & Watson, AJB 2015, 'One-pot homologation of boronic acids: a platform for diversity-oriented synthesis' Organic Letters, vol. 17, no. 24, pp. 6030–6033. https://doi.org/10.1021/acs.orglett.5b03030

One-pot homologation of boronic acids : a platform for diversity-oriented synthesis. / Muir, Calum W.; Vantourout, Julien C.; Isidro-Llobet, Albert; Macdonald, Simon J. F.; Watson, Allan J. B.

In: Organic Letters, Vol. 17, No. 24, 03.12.2015, p. 6030–6033.

Research output: Contribution to journalArticle

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Muir CW, Vantourout JC, Isidro-Llobet A, Macdonald SJF, Watson AJB. One-pot homologation of boronic acids: a platform for diversity-oriented synthesis. Organic Letters. 2015 Dec 3;17(24):6030–6033. https://doi.org/10.1021/acs.orglett.5b03030