Cationic gold(I) complexes are soft Lewis acids able to trigger numerous types of nucleophilic attacks onto alkynes and alkenes. In many cases, the cationic active species is generated directly in the reaction vessel and is not isolated. A convenient way to do so from stable precursors is to use a ligated gold(I) halide and a silver salt. Using the gold-catalyzed hydroalkylation of unactivated alkenes as benchmark reaction, we recently showed that the high efficiency of the halide abstraction by silver salts can be detrimental to the overall efficiency of the catalytic process. Ways to retard the decomposition of the cationic Au(I) species by using derivatives of copper, zinc, indium, bismuth, and other Lewis acids will be presented. We have also developed cationic complexes of gallium able to imitate soft transition metal-based Lewis acids in the catalytic hydroarylation of alkynes. In the second part of the lecture, we will detail the synthesis and the applications of this new kind of π-acid.

Catalytic hydroalkylation and hydroarylation of alkynes and alkenes using gold and gallium π-acids

251st National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.