A New Gold-Catalyzed C—C Bond Formation.
About: This article is published in ChemInform.The article was published on 2000-10-03. It has received 766 citations till now.
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TL;DR: The ability of platinum and gold catalysts to effect powerful atom-economic transformations has led to a marked increase in their utilization and the application of platinum- and gold-catalyzed transformations in natural product synthesis is discussed.
Abstract: The ability of platinum and gold catalysts to effect powerful atom-economic transformations has led to a marked increase in their utilization. The quite remarkable correlation of their catalytic behavior with the available structural data, coordination chemistry, and organometallic reactivity patterns, including relativistic effects, allows the underlying principles of catalytic carbophilic activation by π acids to be formulated. The spectrum of reactivity extends beyond their utility as catalytic and benign alternatives to conventional stoichiometric π acids. The resulting reactivity profile allows this entire field of catalysis to be rationalized, and brings together the apparently disparate electrophilic metal carbene and nonclassical carbocation explanations. The advances in coupling, cycloisomerization, and structural reorganization—from the design of new transformations to the improvement to known reactions—are highlighted in this Review. The application of platinum- and gold-catalyzed transformations in natural product synthesis is also discussed.
1,938 citations
TL;DR: This Review draws on experimental and computational data to present the current understanding of homogeneous gold catalysis, focusing on previously unexplored reactivity and its application to the development of new methodology.
Abstract: Transition-metal catalysts containing gold present new opportunities for chemical synthesis, and it is therefore not surprising that these complexes are beginning to capture the attention of the chemical community. Cationic phosphine-gold(i) complexes are especially versatile and selective catalysts for a growing number of synthetic transformations. The reactivity of these species can be understood in the context of theoretical studies on gold; relativistic effects are especially helpful in rationalizing the reaction manifolds available to gold catalysts. This Review draws on experimental and computational data to present our current understanding of homogeneous gold catalysis, focusing on previously unexplored reactivity and its application to the development of new methodology.
1,534 citations
TL;DR: This critical review summarizes the progress made in this field until November 2006 and describes the development of C-H activation methods for direct functionalization of heterocyclic molecules.
Abstract: During the last two decades there has been considerable growth in the development of catalytic reactions capable of activating unreactive C–H bonds. These methods allow for the synthesis of complex molecules from easily available and cheaper precursors in a fewer number of steps. Naturally, the development of C–H activation methods for direct functionalization of heterocyclic molecules, invaluable building blocks for pharmaceutical and synthetic chemistry and material science, has received substantial attention as well. This critical review summarizes the progress made in this field until November 2006 (117 references).
1,461 citations
TL;DR: Gold catalysis is a very active area in the field of catalysis research, new reactions are published every week, amazing changes in the connectivity are often observed, the number of applications in total synthesis is increasing...--but what are the mechanisms of these reactions?
Abstract: Gold catalysis is a very active area in the field of catalysis research. New reactions are published every week, amazing changes in the connectivity are often observed, the number of applications in total synthesis is increasing...--but what are the mechanisms of these reactions? Sound information can be provided by knowledge about the intermediates of these reactions.
973 citations
TL;DR: In this critical review, the strongly increasing amount of new applications of gold catalysis in total synthesis is summarised and, for the new developed methods, the mode of activation of the substrate by the gold catalyst is discussed.
Abstract: In this critical review, the strongly increasing amount of new applications of gold catalysis in total synthesis is summarised and, for the new developed methods, the mode of activation of the substrate by the gold catalyst is discussed (47 references).
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924 citations