Journal
RSC ADVANCES
Volume 2, Issue 1, Pages 128-131Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c1ra00795e
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- National Science Foundation [CHE-0841611]
- Direct For Mathematical & Physical Scien
- Division Of Chemistry [0841611] Funding Source: National Science Foundation
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The synthesis of alicyclic 3-iminophosphine ligands was extended to include a new framework incorporating a cyclopentenyl backbone with a di-tert-butyl phosphine functionality (3IP(tBu)). The palladium complex [(3IP(tBu))Pd(allyl)]OTf displayed excellent catalytic activity in the 100% atom-efficient hydroamination of 3-methyl-1,2-butadiene (1,1-dimethylallene) with primary aryl amines (anilines), selectively producing the branched allylic amine products (kinetic products) in high conversion at ambient temperature for non-halogenated substrates. Hydroamination using halogenated anilines was successful at 70 degrees C, providing moderate yields, with the formation of little or no linear product (thermodynamic product). Additionally, a subsequent aromatic amino Claisen rearrangement of selected allylic amine products, employing catalytic triflic acid, proved to be an effective atom-economical method for the production of ortho-allylic anilines in a high yielding two-step, one-pot synthesis.
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