Issue 9, 2019

Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates

Abstract

Gold carbene complexes have been recognized as common intermediates in gold-catalyzed organic syntheses. In this field, α-imino gold carbene complexes, in the last few years, have emerged as valuable intermediates toward the synthesis of N-heterocycles. This review is dedicated toward formulating a comprehensive compilation of the different methodologies for heterocyclic synthesis, postulating the participation of α-imino gold carbene complexes as intermediates. In addition to the scarce examples involving the direct formation of α-imino diazo compounds from gold decomposition, the use of nitrogenated nucleophiles, through an initial attack on gold-activated alkynes followed by gold retrodonation and expulsion of a leaving group, constitutes the most commonly employed strategy for achieving this target. This review has been divided into different sections as follows according to the type of N-nucleophile used: azides, aza-ylides, 2H-azirines, isoxazoles and their derivatives, indazoles, and triazapentalenes. A large number of heterocycles, ranging from five- to seven-membered rings, have been efficiently synthesized following this methodology.

Graphical abstract: Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates

Article information

Article type
Review Article
Submitted
09 جمادى الثانية 1440
Accepted
08 رجب 1440
First published
13 رجب 1440

Org. Chem. Front., 2019,6, 1513-1540

Gold-catalyzed heterocyclic syntheses through α-imino gold carbene complexes as intermediates

E. Aguilar and J. Santamaría, Org. Chem. Front., 2019, 6, 1513 DOI: 10.1039/C9QO00243J

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