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- Title
Transition‐Metal‐Free N‐Arylation of Amines by Triarylsulfonium Triflates.
- Authors
Tian, Ze‐Yu; Ming, Xiao‐Xia; Teng, Han‐Bing; Hu, Yu‐Tian; Zhang, Cheng‐Pan
- Abstract
Abstract: A simple and efficient method for transition‐metal‐free N‐arylation of various amines by triarylsulfonium triflates is described. Both aliphatic and aromatic amines were smoothly converted at 80 °C in the presence of tBuOK or KOH to give the corresponding mono N‐arylated products in good to high yields. The molar ratios of the reactants and the choice of bases had a big effect on the reaction. When a large excess of [Ph3S][OTf] and tBuOK were employed for primary amines under the standard conditions, the bis(N‐phenyl) products were predominantly formed. This method was also applicable to the synthesis of bioactive N‐phenyl amino acid derivatives. The control experiments, the deuterium labelling study, and the presence of regioisomers of N‐arylated products when using 4‐substituted triarylsulfonium triflates suggested that the reaction might proceed through an aryne intermediate. The present protocol demonstrated that triarylsulfonium salts are versatile arylation reagents in the construction of CAr−N bonds.
- Subjects
TRANSITION metals; ARYLATION; TRIFLATE compounds; AMINES; AMINO acid derivatives
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 52, p13744
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201802269