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An Active, General, and Long-Lived Palladium Catalyst for Cross-Couplings of Deactivated (Hetero)aryl Chlorides and Bromides with Arylboronic Acids

Takashi Hoshi*, Tomonobu Honma, Ayako Mori, Maki Konishi, Tsutomu Sato, Hisahiro Hagiwara and Toshio Suzuki

*Department of Chemistry and Chemical Engineering, Niigata University, 8050, 2-Nocho, Ikarashi, Nishi-ku, Niigata 950-2181, Japan, Email: hoshigs.niigata-u.ac.jp

T. Hoshi, T. Honma, A. Mori, M. Konishi, T. Sato, H. Hagiwara, T. Suzuki, J. Org. Chem., 2013, 78, 11513-11524.

DOI: 10.1021/jo402089r (free Supporting Information)



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Abstract

An active, general, and long-lived palladium catalyst enables Suzuki-Miyaura reactions of aryl and heteroaryl chlorides deactivated by steric hindrance, electron richness, and coordinating functional groups. The key to the success of the reactions was the development of biphenylene-substituted dicyclohexylruthenocenylphosphine (CyR-Phos) as a supporting ligand.

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Biphenylene-Substituted Ruthenocenylphosphine for Suzuki-Miyaura Coupling of Aryl Chlorides

T. Hoshi, T. Nakazawa, I. Saitoh, Y. Mori, T. Suzuki, J.-i. Sakai, H. Hagiwara, S. Akai, Org. Lett., 2008, 10, 2063-2066.


Key Words

Suzuki Coupling


ID: J42-Y2013