Table
acetylide catalyzed by NiCl2(PPh3)2
3
Couplings of substituted aryl halides and aluminium
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´ ´
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Entry Substrate
1
Product
2
Yieldb (%)
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1
2
(1t)
2t 90
2u 85
(1u)
3
4
(1v)
2v 93
2w 91
(1w)
5
6
a
(1x)
(1y)
2x 92
2y 85
Aryl bromide/Al reagent = 1.0/1.5 mmol; solvent, DME (3 mL).
Isolated yields of products.
b
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benzylic or aryl bromides involving alkynylalane compounds.
The reactions proceeded effectively at room temperature in a
short reaction time of %1 h in the case of substituted benzylic
bromides. The low catalyst loadings of 4 mol% are good enough
to achieve coupling products in excellent yields for substrates
containing strong electron-withdrawing or electron-donating
substituents on the aromatic ring. Furthermore, the coupling
reaction worked efficiently with heterocyclic compound as well.
Financial support from the National Science Council of
Taiwan, ROC, under the grant number of NSC99-2113-M-
005-005-MY3 is appreciated.
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This journal is The Royal Society of Chemistry 2011
Chem. Commun., 2011, 47, 10467–10469 10469