An improved protocol for the preparation of 3-pyridyl- and some arylboronic acids.
TL;DR: 3-Pyridylboronic acid was prepared in high yield and bulk quantity from 3-bromopyridine via a protocol of lithium-halogen exchange and "in situ quench", and this technique was further studied and evaluated on other aryl halides in the preparation of aRYlboronic acids.
Abstract: 3-Pyridylboronic acid was prepared in high yield and bulk quantity from 3-bromopyridine via a protocol of lithium-halogen exchange and "in situ quench". This technique was further studied and evaluated on other aryl halides in the preparation of arylboronic acids.
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TL;DR: Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds Brad M. Rosen, Kyle W. Quasdorf, Daniella A. Wilson, Na Zhang, Ana-Maria Resmerita, Neil K. Garg, and Virgil Percec report on cross-coupling strategies for high-performance liquid chromatography of carbon dioxide and nitrogen.
Abstract: Nickel-Catalyzed Cross-Couplings Involving Carbon-Oxygen Bonds Brad M. Rosen, Kyle W. Quasdorf, Daniella A. Wilson, Na Zhang, Ana-Maria Resmerita, Neil K. Garg,* and Virgil Percec* Roy & Diana Vagelos Laboratories, Department of Chemistry, University of Pennsylvania, Philadelphia, Pennsylvania 19104-6323, United States Department of Chemistry and Biochemistry, University of California, Los Angeles, California 90095, United States
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TL;DR: This review analyses the seven main classes of boron reagent and evaluates the general physical and chemical properties of each class with special emphasis on the currently understood mechanisms of transmetalation.
Abstract: Suzuki–Miyaura (SM) cross-coupling is arguably the most widely-applied transition metal catalysed carbon–carbon bond forming reaction to date. Its success originates from a combination of exceptionally mild and functional group tolerant reaction conditions, with a relatively stable, readily prepared and generally environmentally benign organoboron reagent. A variety of such reagents have been developed for the process, with properties that have been tailored for application under specific SM coupling conditions. This review analyses the seven main classes of boron reagent that have been developed. The general physical and chemical properties of each class of reagent are evaluated with special emphasis on the currently understood mechanisms of transmetalation. The methods to prepare each reagent are outlined, followed by example applications in SM coupling.
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TL;DR: In this article, a direct procedure for Arylboronic Esters was proposed for a cross-coupling reaction of Alkoxydiboron with Haloarenes.
Abstract: G e o r g T h i e m e V e r l a g K G , R ü d i g e r s t r a ß e 1 4 , 7 0 4 6 9 S t u t t g a r t , G e r m a n y 823 T . I S H I Y A M A , M . M U R A T A , N . M I Y A U R A * ( H O K K A I D O U N I V E R S I T Y , S A P P O R O , J A P A N ) Palladium(0)-Catalyzed Cross-Coupling Reaction of Alkoxydiboron with Haloarenes: A Direct Procedure for Arylboronic Esters J. Org. Chem. 1995, 60, 7508–7510.
1,355 citations
TL;DR: In this article, the crosscoupling reaction of (RO)2BB(OR)2 (RO =methoxo and pinacolato) with aryl triflates to give arylsboronates was carried out at 80 °C in the presence of PdCl2(dppf) (3 mol%), dppf(3 mol%) and KOAc (3 equivs) in dioxane.
323 citations
TL;DR: In this article, the methode de Fenske-Hall sur l'anion du borabenzene and ses composes sandwich (BBz) 2 Fe et BBz 2 Co.
15 citations