Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 134, Issue 6, Pages 2906-2909Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja2108992
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Funding
- EPSRC
- Xunta de Galicia [Estadias: 2009/188, 2010/163]
- Engineering and Physical Sciences Research Council [EP/G056609/1] Funding Source: researchfish
- EPSRC [EP/G056609/1] Funding Source: UKRI
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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.
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