Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 74, Issue 4, Pages 1663-1672Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jo802594d
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Funding
- NIH-NIGMS [GM-55382]
- Ministerio de Educacion y Ciencia (Spain)
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The cross-coupling reaction of aryl bromides and iodides with aliphatic and aromatic thiols catalyzed by palladium complexes of the bisphosphine ligand CyPF-tBu (1) is reported. Reactions occur in excellent yields, broad scope, high tolerance of functional groups, and with turnover numbers that exceed those of previous catalysts by 2 or 3 orders of magnitude. These couplings of bromo- and iodoarenes are more efficient than the corresponding reactions of chloroarenes and could be conducted with less catalyst loading and/or milder reaction conditions. Consequently, limitations regarding scope and functional group tolerance previously reported in the coupling of aryl chlorides are now overcome.
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