1359978-79-2Relevant academic research and scientific papers
Activating group recycling in action: A rhodium-catalyzed carbothiolation route to substituted isoquinolines
Arambasic, Milan,Hooper, Joel F.,Willis, Michael C.
supporting information, p. 5162 - 5165 (2013/11/06)
A new rhodium(I) catalyst allows practical and efficient alkyne carbothiolation reactions to be achieved on synthetically useful ketone-bearing aryl methyl sulfides. The carbothiolation adducts, featuring a 'recycled methyl sulfide' activating group, are convenient precursors to highly substituted isoquinolines.
Aryl methyl sulfides as substrates for rhodium-catalyzed alkyne carbothiolation: Arene functionalization with activating group recycling
Hooper, Joel F.,Chaplin, Adrian B.,Gonzalez-Rodriguez, Carlos,Thompson, Amber L.,Weller, Andrew S.,Willis, Michael C.
supporting information; experimental part, p. 2906 - 2909 (2012/03/27)
A Rh(I)-catalyzed method for the efficient functionalization of arenes is reported. Aryl methyl sulfides are combined with terminal alkynes to deliver products of carbothiolation. The overall process results in reincorporation of the original arene functional group, a methyl sulfide, into the products as an alkenyl sulfide. The carbothiolation process can be combined with an initial Rh(I)-catalyzed alkene or alkyne hydroacylation reaction in three-component cascade sequences. The utility of the alkenyl sulfide products is also demonstrated in simple carbo- and heterocycle-forming processes. We also provide mechanistic evidence for the course of this new process.
