References

Three papers that are related to our mechanism:

1. Buarque, C. D.; Pinho, V. D.; Vaz, B. G.; Eberlin, M. N.; da Silva, A. J. M.; Costa, P. R. R. J. Organomet. Chem. 2010, 695, 2062-2067. (This is the link to that paper via UM Library. You will need your UM unique name and passward to gain the access to the paper.)

2. Heck, R. F.; Nolley, J. P. Jr. J. Org. Chem. 1972, 37, 2320-2322. (This is the link to that paper via UM Library. You will need your UM unique name and passward to gain the access to the paper.)

3. Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496-16497. (This is the link to that paper via UM Library. You will need your UM unique name and passward to gain the access to the paper.)

In the journal by Lafrance and Fagnou, the authors studies palladium-catalyzed benzene arylation reaction using pivalic acid as a proton shuttle. The authors found out that the use of the cocatalyst of palladium and pivalic acid greatly increased the yield of arylation products. Another advantage of the cocatalyst is that it can catalyze arylation reaction of unactivated benzene (see Figure above). The palladium catalysis the authors used is Pd(OAc)₂. They also used potassium carbonate as the base. Their reaction conditions are very similar to our reaction. In our reaction, Pd(OAc)₂ was used as the catalyst. Silver carbonate was used as the base instead of potassium carbonate. Pivalic acid was used as the additive. Although our reaction is arylation of cyclobutane instead of benzene, we hypothesize the mechanism should be similar. The use of silver carbonate can form AgI, a precipitate as a product of an intermediate step. Since AgI precipitates out of the reaction, the reaction equilibrium lies to the right, a favorable direction.

Three papers that cite the one above:

1. Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137-3139. (This is the link to that paper via UM Library. You will need your UM unique name and passward to gain the access to the paper.)

The authors chose to cite this because they were studying aerobic biaryl oxidative coupling reactions, which involve forming a new C-C bond from two C-H bonds, a reaction which has greater similarity to the article they cited.

2. Yang, S.; Li, B.; Wan, X.; Shi, Z. J. Am. Chem. Soc. 2007, 129, 6066-6067.(This is the link to that paper via UM Library. You will need your UM unique name and passward to gain the access to the paper.)

The authors chose to cite this as introduction because they were studying ortho arylation with different silyl reagents via C-H activation, which is basically the arylation reaction with a directing group on the substrate.

3. Ackermann, L.; Novak, P.; Vicente, R.; Hofmann, N. Angew. Chem. Int. Ed. 2009, 48, 6045–6048. (This is the link to that paper via UM Library. You will need your UM unique name and passward to gain the access to the paper.)

The authors chose to cite this because the reactivity of ruthenium catalysts in alkylation reaction is similar to that of palladium catalysts in arylation reaction.