Fluoride-Mediated Boronic Acid Coupling Reactions

Wright, Stephen W.; Hageman, David; McClure, Lester D.

doi:10.1021/jo00099a049

Cited by 320 publications

(191 citation statements)

References 0 publications

Supporting

Mentioning

178

Contrasting

Unclassified

Order By: Relevance

“…The cleavage of the boron-carbon bond might be assisted by the acetate ligand of the complex, by forming a neutral leaving species. Because fluoride ion proved to be efficient in other coupling reactions [8,9,10] we performed the transmetallation step with copper(II) fluoride (Fig. 1b).…”

Section: Resultsmentioning

confidence: 99%

“…In most cases the promoter is used in equimolar quantity and also oxygen from air is necessary. Fluoride ions are known to assist the Suzuki [8], Stille [9] and Hiyama [10] cross-coupling reactions, by cleaving the carbonheteroatom bond in the transmetallation step of the reactions. In this article we report the application of copper(II) fluoride reagent in the Chan-Lam-Evans coupling.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Copper(II) Fluoride a New Efficient Promoter of Chan-Lam-Evans Coupling

Komjáti¹,

Szokol

Poppe³

et al. 2015

Period. Polytech. Chem. Eng.

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Copper(II) Fluoride a New Efficient Promoter of Chan-Lam-Evans Coupling

Komjáti¹,

Szokol

Poppe³

et al. 2015

Period. Polytech. Chem. Eng.

View full text Add to dashboard Cite

show abstract

“…19 Unfortunately, the coupling reaction of 6 with boronic acid 4 under anhydrous conditions in the presence of CsF as base 20 only afforded 7 in moderate yield (40-60%). However, the yields compare well with those reported by Lohse, 21 who investigated the reactivity of methyl 4-chloropyridine-2-carboxylate in a Suzuki reaction.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of poly(pyridylthioether) dendrimers incorporating a Fe2(CO)6 cluster core

Chessa¹,

Canovese²,

Visentin³

et al. 2005

Tetrahedron

View full text Add to dashboard Cite

show abstract

“…In some cases, CsF or Bu 4 NF can be used instead of usual bases (eq 5). 5 The Suzuki aromatic aromatic coupling reaction provides all kinds of biaryls selectively in high product yields.…”

Section: Synthesis Of Biarylsmentioning

confidence: 99%

Cross-coupling Reactions of Organoboranes: An Easy Method for C–C Bonding

Suzuki¹,

Yamamoto²

2011

Chemistry Letters

151

View full text Add to dashboard Cite

The palladium-catalyzed cross-coupling reaction between different types of organoboron compounds and various organic halides or triflates in the presence of base provides a powerful and general methodology for the formation of carboncarbon bonds. The Csp 2 B compounds (such as aryl-and 1-alkenylboron derivatives) and Csp 3 B compounds (alkylboron compounds) readily cross-couple with organic electrophiles to give coupled products selectively in high yields. Recently, the CspB compounds (1-alkynylboron derivatives) have been also observed to react with organic electrophiles to produce expected cross-coupled products. The overview of some of such coupling reactions is discussed here in this article. Ç IntroductionCarboncarbon bond formation reactions are important processes in chemistry, because they provide key steps in building complex, bioactive molecules developed as pharmaceuticals and agrochemicals. They are also vital in developing a new generation of ingeniously designed organic materials with novel electronic, optical, or mechanical properties, likely to play a significant role in the burgeoning area of nanotechnology.During the past 40 years, most important carboncarbon bond-forming methodologies have involved using transition metals to mediate the reactions in a controlled and selective manner. The palladium-catalyzed cross-coupling reaction between different types of organoboron compounds and various organic electrophiles including halides or triflates in the presence of base provides a powerful and general methodology for the formation of carboncarbon bonds. Here, some representatives of such reactions are shown in Scheme 1. Numbers in parentheses indicate the years first reported by our group.As one defect of the reaction, one would point out the use of bases. However, the difficulty could be overcome by using suitable solvent systems and adequate bases. Consequently, these coupling reactions have been actively utilized not only in academic laboratories but also in industrial processes. In this paper, three topics, routes to conjugated alkadienes, application to biaryls, and B-alkyl-borane coupling will be discussed. In addition, recent topics will be introduced.Such coupling reactions offer several advantages: (1) Ready availability of reactants. Cross-coupling reactions between vinylic boranes and vinylic halides were not reported to proceed smoothly in the presence of only palladium catalysts. During the initial stage of our exploration, we postulated that a drawback of the coupling is caused by the following aspects of the mechanism. The common mechanism of transition-metal-catalyzed coupling reactions of organometallic compounds with organic halides involves sequential (a) oxidative addition, (b) transmetalation, and (c) reductive elimination.1 It appeared that one of the major reasons that 1-alkenylboranes cannot react with 1-alkenyl halides is step (b). The transmetalation process between RMX (M = transition metal, X = halogen) and organoboranes does not occur readily because of the wea...

show abstract

Fluoride-Mediated Boronic Acid Coupling Reactions

Cited by 320 publications

References 0 publications

Copper(II) Fluoride a New Efficient Promoter of Chan-Lam-Evans Coupling

Copper(II) Fluoride a New Efficient Promoter of Chan-Lam-Evans Coupling

Synthesis of poly(pyridylthioether) dendrimers incorporating a Fe2(CO)6 cluster core

Cross-coupling Reactions of Organoboranes: An Easy Method for C–C Bonding

Contact Info

Product

Resources

About