1370412-47-7Relevant articles and documents
Aryl bromides and aryl chlorides for the direct arylation of benzylic amines mediated by ruthenium(II)
Dastbaravardeh, Navid,Schnuerch, Michael,Mihovilovic, Marko D.
, p. 2878 - 2890 (2013/06/27)
The ruthenium(II)-catalyzed sp3 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 PPh3 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.. Copyright
Ruthenium(0)-catalyzed sp3 C-H bond arylation of benzylic amines using arylboronates
Dastbaravardeh, Navid,Schnuerch, Michael,Mihovilovic, Marko D.
, p. 1930 - 1933 (2012/05/31)
A Ru-catalyzed direct arylation of benzylic sp3 carbons of acyclic amines with arylboronates is reported. This highly regioselective and efficient transformation can be performed with various combinations of N-(2-pyridyl) substituted benzylamines and arylboronates. Substitution of the pyridine directing group in the 3-position proved to be crucial in order to achieve high arylation yields. Furthermore, the pyridine directing group can be removed in high yields via a two-step protocol.
