title: Guanidine/Pd(OAc)2-catalyzed room temperature Suzuki cross-coupling reaction in aqueous media under aerobic conditions.
abstract: A highly efficient Pd(OAc)2/guanidine aqueous system for the room temperature Suzuki cross-coupling reaction has been developed. The new water-soluble and air-stable catalyst Pd(OAc)2.(1f)2 from Pd(OAc)2 and 1,1,3,3-tetramethyl-2-n-butylguanidine (1f) was synthesized and characterized by X-ray crystallography. In the presence of Pd(OAc)2.(1f)2, coupling of arylboronic acids with a wide range of aryl halides, including aryl iodides, aryl bromides, even activated aryl chlorides, was carried out smoothly in aqueous solvent to afford the cross-coupling products in good to excellent yields and high turnover numbers (TONs) (TONs up to 850,000 for the reaction of 1-iodo-4-nitrobenzene and phenylboronic acid). Furthermore, this mild protocol could tolerate a broad range of functional groups.
authors.affiliation: State Key Laboratory of Polymer and Chemistry, Changchun Institute of Applied Chemistry, Changchun 130022, China.
authors.forename: Shenghai
authors.initials: S
authors.lastname: Li
authors.forename: Yingjie
authors.initials: Y
authors.lastname: Lin
authors.forename: Jungang
authors.initials: J
authors.lastname: Cao
authors.forename: Suobo
authors.initials: S
authors.lastname: Zhang