Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 355, Issue 10, Pages 2055-2070Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201300005
Keywords
allenes; cyclometallation; gold catalysis; isoxazoles; propargylic amines
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Funding
- Hong Kong Research Grants Council [PolyU 5027/09P, PolyU 7052/07P]
- Hong Kong Polytechnic University
- Hong Kong Polytechnic University SEG [PolyU01]
- University of Hong Kong (University Development Fund)
- RGC Collaborative Research Fund [HKU1/CRF/08]
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A series of cyclometallated gold(III) complexes [Au(CN)Cl-2] 1a-l (HCN-arylpyridines) and a PEG-linked complex 1m were synthesized. Complexes 1a-m are effective in catalyzing the synthesis of propargylic amines, chiral allenes and isoxazoles. Six-membered ring cyclometallated gold(III) complexes 1f-l exhibited higher catalytic activity than five-membered ring cyclometallated gold(III) complexes 1a-e. The diastereoselectivity of propargylic amines could be tuned by using chiral aldehyde and/ or amine substrates. Excellent enantioselectivities (90-98% ee) were achieved in chiral allene synthesis. Chiral allene racemization could be minimized by using 1f as catalyst. The PEG-linked catalyst 1m is the most catalytically active towards synthesis of propargylic amines, in which case a product turnover of 900 was achieved. Moreover, 1m could be repeatedly used for 12 reaction cycles, leading to an overall turnover number of 872.
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