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

doi:10.1039/C6CC04554E

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

Pure And Applied Chemistry

Research output: Contribution to journal › Article

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.

Language	English
Pages	8703-8706
Number of pages	4
Journal	Chemical Communications
Issue number	56
Early online date	16 Jun 2016
DOIs	10.1039/C6CC04554E
Publication status	Published - 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, C. P., Wilson, K. L., Campbell, A., Mowat, J. M., & Watson, A. J. B. (2016). Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols. Chemical Communications, (56), 8703-8706. https://doi.org/10.1039/C6CC04554E

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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Seath, CP, Wilson, KL, Campbell, A, Mowat, JM & Watson, AJB 2016, 'Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols' Chemical Communications, no. 56, pp. 8703-8706. https://doi.org/10.1039/C6CC04554E

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 journal › Article

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T1 - Synthesis of 2-BMIDA 6,5-bicyclic heterocycles by Cu(I)/Pd(0)/Cu(II) cascade catalysis of 2-iodoaniline/phenols

AU - Seath, Ciaran P.

AU - Wilson, Kirsty L.

AU - Campbell, Angus

AU - Mowat, Jenna M.

AU - Watson, Allan J. B.

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AB - 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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KW - Sonogashira

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KW - aza-derivatives

KW - BMIDA functional group

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