TY - JOUR T1 - Heterogeneous Pd/C-catalyzed ligand-free, room-temperature Suzuki-Miyaura coupling reactions in aqueous media. AU - Maegawa,Tomohiro, AU - Kitamura,Yoshiaki, AU - Sako,Satoko, AU - Udzu,Takahiro, AU - Sakurai,Ai, AU - Tanaka,Asami, AU - Kobayashi,Yusuke, AU - Endo,Koichi, AU - Bora,Utpal, AU - Kurita,Takanori, AU - Kozaki,Atsushi, AU - Monguchi,Yasunari, AU - Sajiki,Hironao, PY - 2007/4/21/pubmed PY - 2007/9/29/medline PY - 2007/4/21/entrez SP - 5937 EP - 43 JF - Chemistry (Weinheim an der Bergstrasse, Germany) JO - Chemistry VL - 13 IS - 20 N2 - A mild and efficient ligand-free Suzuki-Miyaura coupling reaction catalyzed by heterogeneous Pd/C was developed. Aryl bromides and triflates undergo the cross-coupling with aryl boronic acids in excellent yields without the presence of any additives in aqueous media at room temperature. Aryl vinyl boronic acids are also applicable to this coupling reaction and provide the trans-stilbene derivatives in high yields. The application of wet-type Pd/C to the coupling reaction was achieved without any loss of activity under aerobic conditions, and the reuse of Pd/C is feasible for a fifth run without significant loss of activity. Inductively coupled plasma (ICP) mass-spectrometric analysis of the filtrate from the reaction mixture of 4-bromonitrobenzene with phenylboronic acid demonstrated that the palladium metal hardly leached into the solution within the limits of the detector (<1 ppm), thus suggesting that the present Suzuki-Miyaura reaction proceeded by heterogeneous catalysis. SN - 0947-6539 UR - https://www.unboundmedicine.com/medline/citation/17444548/Heterogeneous_Pd/C_catalyzed_ligand_free_room_temperature_Suzuki_Miyaura_coupling_reactions_in_aqueous_media_ L2 - https://doi.org/10.1002/chem.200601795 DB - PRIME DP - Unbound Medicine ER -