Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

Karen Ka‐Yan Kung; Vanessa Kar‐Yan Lo; Hok‐Ming Ko; Gai‐Li Li; Pui‐Ying Chan; King‐Chi Leung; Ming‐Zhong Wang; Chi‐Ming Che

doi:10.1002/adsc.201300005

journal article Jul 08, 2013

Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

Karen Ka‐Yan Kung Vanessa Kar‐Yan Lo Hok‐Ming Ko Gai‐Li Li Pui‐Ying Chan King‐Chi Leung Ming‐Zhong Wang Chi‐Ming Che

Advanced Synthesis & Catalysis Vol. 355 No. 10 pp. 2055-2070 · Wiley

View at Publisher Save 10.1002/adsc.201300005

Abstract

AbstractA series of cyclometallated gold(III) complexes [Au($\widehat{CN}$)Cl2] 1a–l (H$\widehat{CN}$=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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References

182

[1]

[2]

10.1002/ange.200602454

[3]

10.1002/anie.200602454

[4]

10.1038/nature05592

[5]

10.1021/cr000436x

[6]

10.1021/cr068434l

[7]

10.1021/cr068435d

[8]

10.1021/cr0684319

[9]

[10]

10.1021/cr100414u

[11]

10.1021/cr1004088

[12]

[13]

10.1039/c0cs00098a

[14]

de Haro T. Synthesis (2011)

[15]

10.1002/ange.200701521

[16]

10.1002/anie.200701521

[17]

10.1002/ange.201109183

[18]

10.1002/anie.201109183

[19]

10.1002/ange.201204015

[20]

10.1002/anie.201204015

[21]

10.1002/anie.201208777

[22]

[23]

10.1021/ar010065m

[24]

[25]

10.1021/cr068430g

[26]

10.1002/ange.200907078

[27]

10.1002/anie.200907078

[28]

10.1021/ar1000764

[29]

[30]

10.1002/ange.200704729

[31]

10.1002/anie.200704729

[32]

10.1002/chem.200800219

[33]

Pradal A. Synthesis (2011)

[34]

10.1002/asia.201200194

[35]

For coordination of gold(III) complexes see:

[36]

10.1002/ange.200460232

[37]

10.1002/anie.200460232

[38]

10.1002/ange.200462672

[39]

10.1002/anie.200462672

[40]

10.1021/ja066220f

[41]

10.1021/ja0717717

[42]

10.1002/ange.200604746

[43]

10.1002/anie.200604746

[44]

10.1002/adsc.200700209

[45]

10.1021/ja803890t

[46]

10.1002/chem.200701795

[47]

10.1021/ja903863b

[48]

10.1002/ange.200904309

[49]

10.1002/anie.200904309

[50]

10.1016/j.jorganchem.2008.09.058

Showing 50 of 182 references

Cited By

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Recent Developments in the Synthesis and Reactivity of Isoxazoles: Metal Catalysis and Beyond

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Metrics

91

Citations

182

References

Details

Published: Jul 08, 2013
Vol/Issue: 355(10)
Pages: 2055-2070
License: View

Authors

Department of Chemistry the Grubbs Institute Medi-X Pingshan Southern University of Science and Technology Shenzhen 518055 China; State Key Laboratory of Synthetic Chemistry and Department of Chemistry The University of Hong Kong Pokfulam Road Hong Kong China

Cite This Article

Karen Ka‐Yan Kung, Vanessa Kar‐Yan Lo, Hok‐Ming Ko, et al. (2013). Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles. Advanced Synthesis & Catalysis, 355(10), 2055-2070. https://doi.org/10.1002/adsc.201300005

Cyclometallated Gold(III) Complexes as Effective Catalysts for Synthesis of Propargylic Amines, Chiral Allenes and Isoxazoles

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