Let's say I have 2-bromophenyl trifluoromethanesulfonate and I want to perform a Buchwald-Hartwig amination. Would it be possible to selectively modify the OTf with one amine, and THEN the bromide with a second (different) amine?. I guess this should be possible, but haven't seen any paper where they tried to do this. Since I'm here, any suggestions on the base? I've read that Cs2CO3 works better than NaOtBu, particularly with OTf.
Thanks
The power of Reaxys! Found this reference for you. Should be useful.
Espino, Gustavo; Kurbangalieva, Almira; Brown, John M.
Chemical Communications (Cambridge, United Kingdom), 2007 , # 17 p. 1742 - 1744
Thanks a lot Panayiotis. Great reference! By the way, never used Reaxys. I'll have to take a look at it! thanks again.
That is a great paper. Don't know about selectivity but I always find that cesium carbonate/1,4-dioxane is the best base/solvent system for my Buchwald couplings. Palladium(II)acetate and di-tert-butyl(ortho-biphenyl)phosphine are my favorite catalyst/ligand combination by far.
Thanks for the tips on the catalyst and conditions Mark.
I've found another nice reference in addition to that from Panayiotis, just in case you don't have it: J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, S. L. Buchwald, J. Org. Chem. 2000, 65, 1158–1174.
In terms of cost, nonaflates are more cheaper than triflates. Are there any specific reasons why we dont come across aryl nonaflates particularly from the acadamia.
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