Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols

Ciaran P. Seath, Kirsty L. Wilson, Angus Campbell, Jenna M. Mowat, Allan J. B. Watson

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(I)/Pd(0)/Cu(II) catalysis. 2-Iodoanilines and phenols undergo a Cu(I)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(II)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.
LanguageEnglish
Pages8703-8706
Number of pages4
JournalChemical Communications
Issue number56
Early online date16 Jun 2016
DOIs
Publication statusPublished - 18 Jul 2016

Fingerprint

Benzofurans
Indoles
Phenols
Cyclization
Scaffolds
Functional groups
Catalysis
Derivatives
2-iodobenzenamine

Keywords

  • one-pot cascade reaction
  • Sonogashira
  • heterocyclic scaffolds
  • borylated indoles
  • benzofurans
  • aza-derivatives
  • BMIDA functional group

Cite this

Seath, Ciaran P. ; Wilson, Kirsty L. ; Campbell, Angus ; Mowat, Jenna M. ; Watson, Allan J. B. / Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols. In: Chemical Communications. 2016 ; No. 56. pp. 8703-8706.
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abstract = "A one-pot cascade reaction for the synthesis of 2-BMIDA 6,5-bicyclic heterocycles has been developed using Cu(I)/Pd(0)/Cu(II) catalysis. 2-Iodoanilines and phenols undergo a Cu(I)/Pd(0)-catalyzed Sonogashira reaction with ethynyl BMIDA followed by in situ Cu(II)-catalyzed 5-endo-dig cyclization to generate heterocyclic scaffolds with a BMIDA functional group in the 2-position. The method provides efficient access to borylated indoles, benzofurans, and aza-derivatives, which can be difficult to access through alternative methods.",
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Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols. / Seath, Ciaran P.; Wilson, Kirsty L.; Campbell, Angus; Mowat, Jenna M.; Watson, Allan J. B.

In: Chemical Communications, No. 56, 18.07.2016, p. 8703-8706.

Research output: Contribution to journalArticle

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KW - one-pot cascade reaction

KW - Sonogashira

KW - heterocyclic scaffolds

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