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Aryl Bromides and Aryl Chlorides for the Direct Arylation of Benzylic Amines Mediated by Ruthenium(II)
Author(s) -
Dastbaravardeh Navid,
Schnürch Michael,
Mihovilovic Marko D.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201300004
Subject(s) - aryl , chemistry , ruthenium , pyridine , substituent , halide , medicinal chemistry , organic chemistry , combinatorial chemistry , catalysis , alkyl
Abstract The ruthenium(II)‐catalyzed sp 3 C–H bond arylation of benzylic amines with aryl halides is reported. In the present method, aryl iodides and, more importantly, also the cheaper aryl bromides and aryl chlorides can be applied as aryl sources. Additionally, the method does not require elaborate manipulations in a glove box and can be carried out in simple screw cap vials. Potassium pivalate proved to be beneficial for the transformation with aryl bromides or iodides as aryl source, but was not required for aryl chlorides. In the latter case, the addition of PPh 3 led to high conversion. 3‐Methyl and 3‐phenyl pyridine were established as directing groups, and the substituent in the 3‐position represents a key structural feature for high conversion. The directing group can be cleaved after the transformation, which allows access to diarylmethylamines. Mechanistic studies were carried out and critically compared to mechanistic reports of related transformations.