[Reddart]

Looking to react a secondary aliphatic amine with an aryl chloride. The aryl chloride will have weak EWG on it, it that makes any difference. I have used Pd₂dba₃(corrected) DPPF in the past with secondary aryl amines and aryl bromides, but I gather that chlorides are not as reactive as bromides.

[pgk]

Please, take a look to references that concern the aryl chlorides, at the following link:
http://www.princeton.edu/chemistry/macmillan/group-meetings/powerpoint-ian-buchhart.pdf

[kriggy]

Are those couplings generaly aplicable to diamines for ring formation?

[Dan]

Please, take a look to references that concern the aryl chlorides, at the following link:
http://www.princeton.edu/chemistry/macmillan/group-meetings/powerpoint-ian-buchhart.pdf

Reddart, bear in mind that pdf presentation is 13 years out of date and there have been advances since 2002.

I don't know which ligand is best for arylating secondary amines with aryl chlorides, I guess probably P(tBu₃) (Hartwig) of BrettPhos (Buchwald), or even Buchwald's 3rd Gen BrettPhos-Pd precatalyst, but there are a lot of papers on the subject - you just have have to do a literature search for examples closely resembling your system.

[pgk]

I fully agree. Besides, that pdf presentation was an indicative reference and not a detailed literature search up today.