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3.6.15.1 Gold-Catalyzed Reactions of Alkenes

DOI: 10.1055/sos-SD-103-00108

de Haro, T.; Garayalde, D.; Nevado, C.Science of Synthesis Knowledge Updates, (20123171.

The largest developed area in homogeneous gold catalysis comprises the use of gold as a carbophilic Lewis acid due to the strong relativistic effects governing its coordination behavior.[‌1‌‌4‌] Both gold(I) and gold(III) complexes are able to activate unsaturated moieties, triggering a broad palette of transformations.[‌5‌‌11‌]

The term „carbophilic“ is commonly used for gold (as well as for other late transition metals) to emphasize that most of the transformations that involve triple and/or double bonds can be explained by the selective coordination of the metal to the π-electron system. Computational studies have shown that ethene is a slightly better π-donor than acetylene, so that coordination of gold to the π-system of an alkene is a favorable process.[‌12‌‌14‌] Indeed, numerous gold–alkene complexes have been described[‌15‌‌21‌] and studied in solution.[‌22‌,‌23‌] This account focuses on the reactivity aspects stemming from the interaction of gold and alkenes in homogeneous catalysis. Related heterogeneous examples have been reviewed elsewhere[‌24‌,‌25‌] and will thus not be included here. In addition, reactions involving 1,n-enynes and gold, as well as transformations of alkenes triggered by gold redox chemistry have been already covered in Sections 3.6.11.1 and 3.6.13.1, respectively, and thus will not be discussed here in detail.

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