Dual role of carboxylic acid additive: mechanistic studies and implication for the asymmetric C-H amidation

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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.
Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Issue Date
2015-07
Language
English
Article Type
Article
Keywords

N BOND FORMATION; PALLADIUM-CATALYZED ALKYLATION; CARBON-HYDROGEN BONDS; UNACTIVATED ARENES; ROOM-TEMPERATURE; DIRECTING GROUPS; MILD CONDITIONS; NITROGEN-SOURCE; AMINO-ACIDS; ACTIVATION

Citation

TETRAHEDRON, v.71, no.26-27, pp.4504 - 4511

ISSN
0040-4020
DOI
10.1016/j.tet.2015.02.065
URI
http://hdl.handle.net/10203/199995
Appears in Collection
CH-Journal Papers(저널논문)
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