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Recent Advances in the Gold-catalyzed Additions to C-C Multiple Bonds

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Specialty Chemistry
Date 2011 Aug 2
PMID 21804887
Citations 14
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Abstract

C-O, C-N and C-C bonds are the most widespread types of bonds in nature, and are the cornerstone of most organic compounds, ranging from pharmaceuticals and agrochemicals to advanced materials and polymers. Cationic gold acts as a soft and carbophilic Lewis acid and is considered one of the most powerful activators of C-C multiple bonds. Consequently, gold-catalysis plays an important role in the development of new strategies to form these bonds in more convenient ways. In this review, we highlight recent advances in the gold-catalyzed chemistry of addition of X-H (X = O, N, C) bonds to C-C multiple bonds, tandem reactions, and asymmetric additions. This review covers gold-catalyzed organic reactions published from 2008 to the present.

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References
1.
Hopkinson M, Ross J, Giuffredi G, Gee A, Gouverneur V . Gold-catalyzed cascade cyclization-oxidative alkynylation of allenoates. Org Lett. 2010; 12(21):4904-7. DOI: 10.1021/ol102061k. View

2.
Ye L, Cui L, Zhang G, Zhang L . Alkynes as equivalents of alpha-diazo ketones in generating alpha-oxo metal carbenes: a gold-catalyzed expedient synthesis of dihydrofuran-3-ones. J Am Chem Soc. 2010; 132(10):3258-9. PMC: 2847863. DOI: 10.1021/ja100041e. View

3.
Cordonnier M, Blanc A, Pale P . Gold(I)-catalyzed rearrangement of alkynyloxiranes: a mild access to divinyl ketones. Org Lett. 2008; 10(8):1569-72. DOI: 10.1021/ol800219k. View

4.
Ruttinger R, Leutzow J, Wilsdorf M, Wilckens K, Czekelius C . Reversal of selectivity in gold-catalyzed cyclizations of 3,3-disubstituted 1,4-diynes. Org Lett. 2010; 13(2):224-7. DOI: 10.1021/ol102628x. View

5.
Wang Y, Zhu L, Zhang Y, Chen Z . Diastereoselective gamma-vinyl butyrolactone synthesis via gold catalyzed cyclization of allylic acetate. Chem Commun (Camb). 2010; 46(4):577-9. DOI: 10.1039/b913348h. View