Abstract
Acid additive effects in the Ir-catalyzed C-H amidation of arylphosphoryl compounds were examined. Structure of catalytically active metal species was elucidated: mono-cationic iridium catalyst [Cp∗Ir(III)(OAc)](NTf2) being mainly responsible for the C-H bond activation. Mechanistic studies revealed a dual role of carboxylic acid additive operating both in the generation of an iridacyclic intermediate and in the protodemetalation process to release amidated products. The fact that asymmetric C-H amidation was achieved albeit in moderate enantioselectivity by using chiral carboxylic acid supports our proposal especially with regard to the role of acid additive.
Original language | English |
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Pages (from-to) | 4504-4511 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 71 |
Issue number | 26-27 |
DOIs | |
State | Published - 30 May 2015 |
Externally published | Yes |
Keywords
- Acid additive effects
- Asymmetric induction
- C-H amidation
- Mechanistic study
- Phosphoryl compounds