Gold-Catalyzed Reactions of Cyclopropenes

Patai's Chemistry of Functional Groups Pub Date : 2015-03-25 DOI:10.1002/9780470682531.PAT0803

Alexis Archambeau, Frédéric Miege, J. Cossy, C. Meyer

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引用次数: 1

Abstract

Cyclopropenes have often been used as substrates in transition metal-promoted or catalyzed reactions. Since the first reports in 2008, gold-catalyzed reactions of cyclopropenes have rapidly evolved to an active research field. The observed reactivity is essentially related to the ability of cyclopropenes to undergo ring-opening in the presence of gold(I) complexes and hence generate alkenyl gold carbenoids. These latter organogold species act as key reactive catalytic entities in a wide range of transformations including inter- or intramolecular nucleophilic additions of heteroatom or carbon nucleophiles, carbene-type coupling reactions and olefin cyclopropanations. Additionally, cyclopropenes can also behave as π nucleophiles in gold-catalyzed enyne cycloisomerizations wherein alkynes are preferentially activated by gold(I) complexes. A wide variety of acyclic and cyclic products can be produced by these gold-catalyzed reactions of cyclopropenes and the different contributions as well as the theoretical studies in this field have been summarized in this chapter. Keywords: carbenoids; catalysis; cyclopropanation; cyclopropenes; gold complexes; nucleophilic additions; rearrangement; ring-opening

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环丙烯的金催化反应

环丙烯常被用作过渡金属促进或催化反应的底物。自2008年首次报道以来，金催化环丙烯的反应迅速发展成为一个活跃的研究领域。所观察到的反应活性本质上与环丙烯在金(I)配合物存在下开环的能力有关，从而产生烯基金类碳。这些后一种有机金在广泛的转化中起着关键的催化作用，包括杂原子或碳亲核试剂的分子间或分子内亲核加成、碳型偶联反应和烯烃环丙烷化。此外，环丙烯在金催化的炔环异构化反应中也表现为π亲核试剂，其中炔优先被金(I)配合物激活。金催化环丙烯的这些反应可以产生各种各样的无环和环产物，本章对这一领域的不同贡献和理论研究进行了总结。关键词:carbenoids;催化;摘要总结;cyclopropenes;黄金情结;亲核的增加;重排;开环

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Patai's Chemistry of Functional Groups

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