The Cited Article for Negishi cross-coupling reaction
Milne, J. E.; Buchwald, S. L. J. Am. Chem. Soc., 2004, 126, 13028-13032
This article investigates a different protocol that is supposed to allow for more efficient cross-coupling. Specifically, a new method of Negishi cross-coupling of organozinc reagents with aryl halides has been perfected which doesn’t require as much palladium catalyst as before, and the product is stable with a wide range of functional groups. In finding good ligands for the palladium, phosphine was found to be a good stabilizer as part of the ligand; however, usage of the phosphine ligand led to lower yield of the desired product. This was counteracted by increasing the size of the substituent on the lower aromatic ring of the phosphine ligand which led to a more productive reaction. By comparing the difference between the inclusion of one halide instead of two halides as part of the ligand, increasing the electron density of the aromatic portion was found to increase catalyst activity. The article then goes on to investigate a protocol for biaryldialkylphosphine ligands, the most useful ligands in this case.
The Citing Articles
Patel, N. D.; Sieber, J. D.; Tcyrulnikov, S.; Simmons, B. J.; Rivalti, D.; Duvvuri, K.; Zhang, Y.; Gao Y. A.; Fandrick, K. R.; Haddad, N.; Lao, K. S.; Mangunuru, H. P. R.; Biswas, S.; Qu, B.; Grinberg, N.; Pennino, S.; Lee, H.; Song, J. J.; Gupton, B. F.; Garg, N. K.; Kozlowski, M. C.; Senanayake C. H. ACS Catal., 2018, 8, 10190–10209.
This article investigates Negishi cross-coupling in the context of the regioselectivity of ortho to the functional group.
Devendar, P.; Qu, R.; Kang, W,; He, B.; Yang G. J. Agric. Food Chem., 2018, 66, 8914–8934.
This article compares Negishi cross-coupling to the Suzuki, Stille, Sonogashira, Suzuki, and Heck reactions in the industrial application of producing cross-coupled organic agrochemicals. The article argues Negishi cross-coupling the halide and zinc required introduce instability that is not preferred in an industrial setting.
Zhang, K.; Christoffel, F.; Baudin, O. Angewandte Chemie I.E., 2018, 57, 1982-1986.
This article explains the development of a new Negishi cross-coupling of specifically secondary alkyl bromides with aryl and alkenyl triflates and nonaflates.