Recent advances in the gold-catalyzed additions to C–C multiple bonds

Abstract

SummaryC–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.

Ring Expansions of Activated Aziridines and Azetidines

“…Gold-catalyzed cycloisomerization reaction of alkynyl aziridines produces 2,5-disubstituted pyrroles in high yields [100,[104][105][106]. Extending this synthetic protocol Hou and co-workers synthesized a range of 2,5-disubstituted pyrroles 211 in high yields from alkynyl aziridines 210.…”

Iron(III) Triflimide as a Catalytic Substitute for Gold(I) in Hydroaddition Reactions to Unsaturated Carbon–Carbon Bonds

“…Modern organic synthesis based on catalysis by transition metals has increased its possibilities with the introduction of gold for making new carbon-carbon and carbon-heteroatom bonds. [1][2][3][4][5][6][7][8][9][10][11][12][13] Nonetheless, there is much incentive to substitute expensive and toxic heavy late transition metals by cheaper, widely available, and environmentally-friendly first-row transition metals, such as iron. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] The aim of our work here is to study iron, gold, and triflimidic acid, representative examples of first-row and heavy late transition metals and Brønsted acids, respectively, as catalysts for hydroaddition reactions to p-carbophilic unsaturated CÀC bonds (alkenes and alkynes) of carbon, oxygen, nitrogen, and sulfur nucleophiles, a set of complete atom-economical reactions with growing potential in organic synthesis.…”

Gold-Catalyzed Synthesis of 2-Sulfenylspiroindolenines via Spirocyclizations

“…The reaction mixture was stirred for 4 h at room temperature. Then a saturated aqueous solution of NH 4 Cl was added before to pour the reaction media in a separatory funnel containing ethyl acetate. After separation of the phases the aqueous phase was extracted twice with ethyl acetate, then the combined organic phases were washed twice with water and with brine.…”

“…Gold complexes are highly effective catalysts to trigger the addition of nucleophiles to alkynes [1][2][3][4][5][6]. Over the last few years, the functionalization of indoles using gold catalysis has stimulated very active research in the fields of catalysis and organic synthesis.…”