Mechanistic analysis of gold(I)-catalyzed intramolecular allene hydroalkoxylation reveals an off-cycle bis(gold) vinyl species and reversible C-O bond formation.

作者: Timothy J. Brown , Dieter Weber , Michel R. Gagné , Ross A. Widenhoefer

DOI: 10.1021/JA303844H

关键词:

摘要: Mechanistic investigation of gold(I)-catalyzed intramolecular allene hydroalkoxylation established a mechanism involving rapid and reversible C–O bond formation followed by turnover-limiting protodeauration from mono(gold) vinyl complex. This on-cycle pathway competes with catalyst aggregation an off-cycle bis(gold)

参考文章(34)
Norbert Krause, Christian Winter, Gold-catalyzed nucleophilic cyclization of functionalized allenes: a powerful access to carbo- and heterocycles. Chemical Reviews. ,vol. 111, pp. 1994- 2009 ,(2011) , 10.1021/CR1004088
Rebecca L. LaLonde, Benjamin D. Sherry, Eun Joo Kang, F. Dean Toste, Gold(I)-catalyzed enantioselective intramolecular hydroamination of allenes. Journal of the American Chemical Society. ,vol. 129, pp. 2452- 2453 ,(2007) , 10.1021/JA068819L
Paul Ha-Yeon Cheong, Philip Morganelli, Michael R. Luzung, K. N. Houk, F. Dean Toste, Gold-catalyzed cycloisomerization of 1,5-allenynes via dual activation of an ene reaction. Journal of the American Chemical Society. ,vol. 130, pp. 4517- 4526 ,(2008) , 10.1021/JA711058F
Le-Ping Liu, Gerald B. Hammond, Recent advances in the isolation and reactivity of organogold complexes Chemical Society Reviews. ,vol. 41, pp. 3129- 3139 ,(2012) , 10.1039/C2CS15318A
Zhibin Zhang, Christopher F. Bender, Ross A. Widenhoefer, Gold(I)-Catalyzed Dynamic Kinetic Enantioselective Intramolecular Hydroamination of Allenes Journal of the American Chemical Society. ,vol. 129, pp. 14148- 14149 ,(2007) , 10.1021/JA0760731
Matthias Rudolph, A. Stephen K. Hashmi, Heterocycles from gold catalysis. Chemical Communications. ,vol. 47, pp. 6536- 6544 ,(2011) , 10.1039/C1CC10780A
Dieter Weber, Michel R. Gagné, Dinuclear gold-silver resting states may explain silver effects in gold(I)-catalysis. Organic Letters. ,vol. 11, pp. 4962- 4965 ,(2009) , 10.1021/OL902116B
A. Stephen K. Hashmi, Homogeneous gold catalysis beyond assumptions and proposals--characterized intermediates. Angewandte Chemie. ,vol. 49, pp. 5232- 5241 ,(2010) , 10.1002/ANIE.200907078
Zhibin Zhang, Christopher F. Bender, Ross A. Widenhoefer, Gold(I)-catalyzed enantioselective hydroamination of N-allenyl carbamates. Organic Letters. ,vol. 9, pp. 2887- 2889 ,(2007) , 10.1021/OL071108N