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

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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.

Original language	English
Pages (from-to)	8703-8706
Number of pages	4
Journal	Chemical Communications
Issue number	56
Early online date	16 Jun 2016
DOIs	https://doi.org/10.1039/C6CC04554E
Publication status	Published - 18 Jul 2016

Keywords

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

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10.1039/C6CC04554E

Seath-etal-CC2016-Synthesis-of-2-BMIDA-6-5-bicyclic-heterocyclesAccepted author manuscript, 3.19 MB

Cite this

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

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.",

keywords = "one-pot cascade reaction, Sonogashira, heterocyclic scaffolds, borylated indoles, benzofurans, aza-derivatives, BMIDA functional group",

author = "Seath, {Ciaran P.} and Wilson, {Kirsty L.} and Angus Campbell and Mowat, {Jenna M.} and Watson, {Allan J. B.}",

year = "2016",

month = jul,

day = "18",

doi = "10.1039/C6CC04554E",

language = "English",

pages = "8703--8706",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "56",

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TY - JOUR

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.

PY - 2016/7/18

Y1 - 2016/7/18

N2 - 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.

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.

KW - one-pot cascade reaction

KW - Sonogashira

KW - heterocyclic scaffolds

KW - borylated indoles

KW - benzofurans

KW - aza-derivatives

KW - BMIDA functional group

UR - http://pubs.rsc.org/en/journals/journalissues/cc

U2 - 10.1039/C6CC04554E

DO - 10.1039/C6CC04554E

M3 - Article

SP - 8703

EP - 8706

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 56

ER -

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

Abstract

Keywords

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