Please use this identifier to cite or link to this item: http://hdl.handle.net/10397/34224
Title: Cyclometallated gold(III) complexes as effective catalysts for synthesis of propargylic amines, chiral allenes and isoxazoles
Authors: Kung, KKY
Lo, VKY
Ko, HM
Li, GL
Chan, PY
Leung, KC
Zhou, Z
Wang, MZ
Che, CM
Wong, MK 
Keywords: Allenes
Cyclometallation
Gold catalysis
Isoxazoles
Propargylic amines
Issue Date: 2013
Publisher: Wiley-V C H Verlag Gmbh
Source: Advanced synthesis and catalysis, 2013, v. 355, no. 10, p. 2055-2070 How to cite?
Journal: Advanced Synthesis and Catalysis 
Abstract: A series of cyclometallated gold(III) complexes [Au(CN)Cl2] 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.
URI: http://hdl.handle.net/10397/34224
ISSN: 1615-4150
DOI: 10.1002/adsc.201300005
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