Litcius/Paper detail

Nitrene Transfer and Carbene Transfer in Gold Catalysis

Long‐Wu Ye, Xin‐Qi Zhu, Rajkumar Lalji Sahani, Yin Xu, Peng‐Cheng Qian, Rai‐Shung Liu

2020Chemical Reviews387 citationsDOI

Abstract

Catalytic transformations involving metal carbenes are considered one of the most important aspects of homogeneous transition metal catalysis. Recently, gold-catalyzed generation of gold carbenes from readily available alkynes represents a significant advance in metal carbene chemistry. This Review summarizes the advances in the gold-catalyzed nitrene-transfer reactions of alkynes with nitrogen-transfer reagents, such as azides, nitrogen ylides, isoxazoles, and anthranils, and gold-catalyzed carbene-transfer reactions, involving oxygen atom-transfer reactions of alkynes with nitro compounds, nitrones, sulfoxides, and pyridine N-oxides, through the presumable α-imino gold carbene and α-oxo gold carbene intermediates, respectively. Gold-catalyzed processes are reviewed by highlighting their product diversity, selectivity, and applicability, and the mechanistic rationale is presented where possible.

Topics & Concepts

NitreneCarbeneChemistryCatalysisCombinatorial chemistryPhotochemistryTransfer hydrogenationPyridineOrganic chemistryRutheniumCatalytic Alkyne ReactionsCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms