Gold-Catalyzed Reactions of Specially Activated Alkynes, Allenes, and Alkenes.

Autor: Campeau D; Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5 Ottawa, Canada., León Rayo DF; Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5 Ottawa, Canada., Mansour A; Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5 Ottawa, Canada., Muratov K; Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5 Ottawa, Canada., Gagosz F; Department of Chemistry and Biomolecular Sciences, University of Ottawa, K1N 6N5 Ottawa, Canada.
Jazyk: angličtina
Zdroj: Chemical reviews [Chem Rev] 2021 Jul 28; Vol. 121 (14), pp. 8756-8867. Date of Electronic Publication: 2020 Nov 23.
DOI: 10.1021/acs.chemrev.0c00788
Abstrakt: This review describes the gold-catalyzed reactions of specially activated alkynes, allenes, and alkenes. Such species are characterized by the presence of either electron-donating or electron-withdrawing groups as substituents of the carbon π-system. They are intrinsically polarized, and when compared to their nonspecially activated counterparts can therefore be involved in gold-catalyzed transformations featuring increased regio-, stereo-, and chemoselectivities. The chemistry of specially activated carbon π-systems under homogeneous gold catalysis is extremely rich and varied. The reactivity observed with nonspecially activated unsaturated systems can often be transposed to specially activated ones without loss of efficiency. However, specially activated carbon π-systems also exhibit specific reactivities that cannot be attained with regular substrates. In this family of carbon π-systems, ynamides and their analogs, along with alkynyl carbonyl derivatives, are the classes of substrates that have retained the most attention. This review provides an overview of the chemistry developed with all classes of specially activated carbon π-systems by discussing their general and specific reactivities, presenting and commenting on their gold-catalyzed transformations as well as their applications.
Databáze: MEDLINE