Guanidine/Pd(OAc)(2)-catalyzed room temperature Suzuki cross-coupling reaction in aqueous media under aerobic conditions
摘要:
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.
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关键词:
HETEROCYCLIC CARBENE LIGANDS HINDERED ARYL CHLORIDES CATALYZED HECK REACTION HIGHLY EFFICIENT PALLADIUM NANOPARTICLES ARYLBORONIC ACIDS PHOSPHINE-LIGANDS MILD CONDITIONS IONIC LIQUIDS MIYAURA REACTIONS
年份:
2007

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