C–H and C–F Bond Activations at a Rhodium(I) Boryl Complex: Reaction Steps for the Catalytic Borylation of Fluorinated Aromatics

Kalläne, Sabrina I.; Teltewskoi, Michael; Braun, Thomas; Braun, Beatrice

doi:10.1021/om500952x

Cited by 90 publications

(53 citation statements)

References 132 publications

(84 reference statements)

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“…102 The Rh(H)(PEt 3 ) 3 also activates the C-H bonds of fluorinated benzenes and pyridines. [182][183][184] The germyl complex reacts with pentafluorobenzene and 2,3,5,6-tetrafluoropyridine by C-H activation. 185 Activation of C-H bonds has been studied at the iridium pentahydride complex trans- (Figure 17).…”

Section: Scheme 3 the Five Primary Reactive Channels Describing The mentioning

confidence: 99%

Selectivity of C–H Activation and Competition between C–H and C–F Bond Activation at Fluorocarbons

2017

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Partially fluorinated alkanes, arenes, and alkenes can be transformed by a variety of transition metal and lanthanide systems. Although the C-H bond is weaker than the C-F bond regardless of the hybridization of the carbon, the reaction of the C-F bond at the metal is usually more exothermic than the corresponding reaction of the C-H bonds. Both bonds are activated by the metal systems, but the preference for activating these bonds depends on the nature of the hydrocarbon and of the metal system, so that the reaction can be directed exclusively toward C-H or C-F bonds or yield a mixture of products. Additionally, the presence of fluorine differentiates between C-H bonds at different positions resulting in regioselective C-H bond activation; paradoxically, the strongest C-H bond reacts preferentially. The purpose of this review is to describe the field of reactions of partially fluorinated substrates with transition metal atoms, ions, and molecular complexes. The controlling physical properties (thermodynamics and kinetics) are described first, followed by a description of stoichiometric reactions, with the competition between the C-H and C-F activations as focus. A few representative catalytic systems are discussed. The review also highlights the benefit of combining experimental and theoretical studies.

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Section: Scheme 3 the Five Primary Reactive Channels Describing The mentioning

confidence: 99%

Selectivity of C–H Activation and Competition between C–H and C–F Bond Activation at Fluorocarbons

2017

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“…4 Reactions that transform an unreactive carbon–fluorine bond to a reactive and polarized carbon–element bond (element = boron, aluminum, silicon) are gaining increasing attention. 5−8 …”

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Addition of Carbon–Fluorine Bonds to a Mg(I)–Mg(I) Bond: An Equivalent of Grignard Formation in Solution

2016

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“…This approach represents a method for directly generating reactive intermediates from non-reactive chemical feedstocks, that uses the most abundant metal in the earth's crust without the need for expensive or toxic transition metal catalysts. 12 , 13 …”

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confidence: 99%

Oxidative addition of carbon–fluorine and carbon–oxygen bonds to Al(i)

2015

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C–H and C–F Bond Activations at a Rhodium(I) Boryl Complex: Reaction Steps for the Catalytic Borylation of Fluorinated Aromatics

Abstract: Treatment of the rhodium(I) boryl complex [Rh(Bpin)(PEt 3 ) 3 ] (1, pin = pinacolato = O 2 C 2 Me 4 ) with pentafluorobenzene,

Cited by 90 publications

References 132 publications

Selectivity of C–H Activation and Competition between C–H and C–F Bond Activation at Fluorocarbons

Selectivity of C–H Activation and Competition between C–H and C–F Bond Activation at Fluorocarbons

Addition of Carbon–Fluorine Bonds to a Mg(I)–Mg(I) Bond: An Equivalent of Grignard Formation in Solution

Oxidative addition of carbon–fluorine and carbon–oxygen bonds to Al(i)

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