Abstract
Language | English |
---|---|
Pages | 8703-8706 |
Number of pages | 4 |
Journal | Chemical Communications |
Issue number | 56 |
Early online date | 16 Jun 2016 |
DOIs | |
Publication status | Published - 18 Jul 2016 |
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Keywords
- one-pot cascade reaction
- Sonogashira
- heterocyclic scaffolds
- borylated indoles
- benzofurans
- aza-derivatives
- BMIDA functional group
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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 journal › Article
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
T2 - Chemical Communications
JF - Chemical Communications
SN - 1359-7345
IS - 56
ER -