Cross coupling reactions of polyfluoroarenes via C–F activation

Sun, Alex D.; Love, Jennifer A.

doi:10.1039/c0dt00540a

Cited by 218 publications

(73 citation statements)

References 90 publications

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“…Thus, hydrodefluorination or cross coupling reactions can provide fluorinated building blocks, which are often not accessible otherwise . However, catalytic C-F bond functionalization reactions of highly fluorinated aromatic precursors via cross coupling reactions are still rare [4,14,17,[23][24][25][32][33][34][35][36][37][38][39][40][41][42][43][44][45][46][47]. Radius et al reported an initial and exceptional example of a nickelmediated Suzuki-Miyaura cross coupling reaction of perfluorotoluene with aryl boronic acids on using a nickel(II) carbene complex as catalyst [25].…”

Section: Introductionmentioning

confidence: 99%

Nickel fluoro complexes as intermediates in catalytic cross-coupling reactions

Breyer

Berger

Braun

et al. 2012

Journal of Fluorine Chemistry

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Section: Introductionmentioning

confidence: 99%

Nickel fluoro complexes as intermediates in catalytic cross-coupling reactions

Breyer

Berger

Braun

et al. 2012

Journal of Fluorine Chemistry

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“…5,6 Braun has successfully carried out nickelcatalyzed Stille 7,8 and Suzuki 9 coupling reactions of several perfluoroheteroaromatic derivatives, pentafluoropyridine and 2,4,6-trifluoro-5-chloropyrimidine, respectively. Radius has also reported similar Suzuki cross -coupling reactions between octafluorotoluene and decafluorobiphenyl and various electron rich aryl boronic acid derivatives in which the C-F bond para to the trifluoromethyl or pentafluorophenyl group was activated and fluorine displaced by an aryl group.…”

Section: Introductionmentioning

confidence: 99%

Pd-catalyzed sp2–sp cross-coupling reactions involving C–F bond activation in highly fluorinated nitrobenzene systems

Cargill¹,

Sandford²,

Kılıçkıran³

et al. 2013

Tetrahedron

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Nelles, G. (2013) 'Pd-catalysed sp2-sp cross-coupling reactions involving aromatic C-F bond activation in highly uorinated nitrobenzene systems.', Tetrahedron., 69 (2). pp. 512-516. Further information on publisher's website:http://dx.doi.org/10.1016/j.tet.2012.11.031Publisher's copyright statement: NOTICE: this is the author's version of a work that was accepted for publication in Tetrahedron. Changes resulting from the publishing process, such as peer review, editing, corrections, structural formatting, and other quality control mechanisms may not be reected in this document. Changes may have been made to this work since it was submitted for publication. A denitive version was subsequently published in Tetrahedron, 69, 2, 2013Tetrahedron, 69, 2, , 10.1016Tetrahedron, 69, 2, /j.tet.2012.031. Additional information:Use policyThe full-text may be used and/or reproduced, and given to third parties in any format or medium, without prior permission or charge, for personal research or study, educational, or not-for-prot purposes provided that:• a full bibliographic reference is made to the original source • a link is made to the metadata record in DRO • the full-text is not changed in any way The full-text must not be sold in any format or medium without the formal permission of the copyright holders.Please consult the full DRO policy for further details. Abstract-Direct and regioselective alkynylation of highly fluorinated nitrobenzene derivatives by palladium-catalyzed Sonogashira type processes is described, representing the first examples of metal-catalyzed sp 2 -sp cross-coupling reactions involving C-F bond activation.

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“…So, the selective cleavage of one or several C-F bonds in those molecules followed by a suitable functionalization is a way to obtain partially fluorinated compounds of high interest. Reviews with an extensive coverage of the subjects of C-F activation, 6,7,[224][225][226] and fluorination 10,227,228 are available in the literature. The purpose of this section is to cover palladium mediated processes in the area.…”

Section: C-f Activation and Fluorinationmentioning

confidence: 99%