In that reaction, which catalyst or reaction condition is the best way to go?
Although I haven't done a Yamamoto myself, and it's with Ni, I can tell you from our experience with Stille cross-couplings, that a Nitrogen adjacent to the Br (in ortho) is a big problem. We have an example for this in J. Linshoeft, A.C.J. Heinrich, S.A.W. Segler, P.J. Gates and A. Staubitz, Org. Lett. 2012 , 14, 5644-5647. See entries 4 and 5. I attach it for you. We speculated that the N complexes the catalyst, but of course, there is no direct proof. However, we see this problem with many N containing aromatic heterocycles: They can be very stubborn in cross-coupling reactions!
Dr. Staubitz,
Thank you very much for your kind answer. Do you think that useing stoichiometric amount of catalyst instead of catalytic might be a solution in order to overcome the complex forming.
Thank you.
N on the 2-bromopyridine make the compound more reactive towards Yamamoto coupling reactions compared to reqular bromo benzene as C-Br bond is made weakerdue to electron withdrawing effect of nitrogen.
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