Abstract
The rational design and synthesis of a novel dialkylbiarylphosphine ligand, 2′-(dimethylphosphine)-2,6-dimethoxy-1,1′-biphenyl (MeSPhos), for palladium-catalyzed C–N cross-coupling reactions is described. Based on previous results, it was hypothesized that a ligand with electronic properties similar to (2-biphenyl)dimethylphosphine (MeJPhos) but with greater steric bulk would allow the cross-coupling of previously inaccessible deactivated aryl chlorides. As predicted, MeSPhos exhibited similar electronic properties to MeJPhos. However, MeSPhos surprisingly showed a significantly smaller steric profile than MeJPhos. In comparison to the widely used CySPhos (2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl), MeSPhos promoted the oxidative addition of highly deactived aryl chlorides for which CySPhos was ineffective, but significantly decreased the rate of reductive elimination. The kinetics of cross-coupling reactions showed that the altered steric and electronic parameters of MeSPhos had a significant impac...
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