Oxime-derived chloro-bridged palladacycles 12 and 13 are efficient complexes for the Suzuki-Miyaura reactions of aryl-, allyl-, and benzyl halides with arylboronic acids. The isolated catalysts are thermally stable, not sensitive to air or moisture, and easily accessible from inexpensive starting materials. The reaction can be performed under aerobic conditions with aryl bromides and chlorides, displaying turnover numbers (TON) of up to 5× 105 and ...
[Semmelhack, M.F.; Helquist, Paul; Jones, L.D.; Keller, Leonard; Mendelson L.; et al. Journal of the American Chemical Society, 1981 , vol. 103, # 21 p. 6460 - 6471]