Palladium(III)-Catalyzed Fluorination of Arylboronic Acid Derivatives

Mazzotti, Anthony R.; Campbell, Michael G.; Tang, Pingping; Murphy, Jennifer M.; Ritter, Tobias

doi:10.1021/ja405919z

Cited by 147 publications

(72 citation statements)

References 42 publications

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“…In 2013, Mazzotti et al developed palladium-III -catalyzed fluorination of aryl boronic acids ( Figure 5). 21 Unlike the previously reported Pd-mediated fluorination, 13,19 the C-F bond formation presented here seems to proceed without the formation of organopalladium complexes. The author proposed a single-electron-transfer (SET) mechanism involving a well-defined Pd III 3 .…”

contrasting

confidence: 73%

Recent advances in green fluorine chemistry

Zeng¹,

Hu²

2015

ROC

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contrasting

confidence: 73%

Recent advances in green fluorine chemistry

Zeng¹,

Hu²

2015

ROC

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“…112 In 2013, Ritter and co-workers reported the fluorination of arylboronic acids using Pd(II) complex 75 (Scheme 58). 157 Selectfluor occurs to afford Pd(III) species 77 ( Figure 4) and a SelectoFluor radical cation. Subsequent F· transfer to the ipso position of an aryl trifluoroborate forms the C−F bond by generating delocalized radical 78.…”

Section: Carbon−halogen Reductive Elimination From Pd(iii) Complexesmentioning

confidence: 99%

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

2016

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The high utility of halogenated organic compounds has prompted the development of a vast number of transformations which install the carbon-halogen motif. Traditional routes to these building blocks have commonly involved multiple steps, harsh reaction conditions, and the use of stoichiometric and/or toxic reagents. In this regard, using transition metals to catalyze the synthesis of organohalides has become a mature field in itself, and applying these technologies has allowed for a decrease in the production of waste, higher levels of regio- and stereoselectivity, and the ability to produce enantioenriched target compounds. Furthermore, transition metals offer the distinct advantage of possessing a diverse spectrum of mechanistic possibilities which translate to the capability to apply new substrate classes and afford novel and difficult-to-access structures. This Review provides comprehensive coverage of modern transition metal-catalyzed syntheses of organohalides via a diverse array of mechanisms. Attention is given to the seminal stoichiometric organometallic studies which led to the corresponding catalytic processes being realized. By breaking this field down into the synthesis of aryl, vinyl, and alkyl halides, it becomes clear which methods have surfaced as most favored for each individual class. In general, a pronounced shift toward the use of C-H bonds as key functional groups, in addition to methods which proceed by catalytic, radical-based mechanisms has occurred. Although always evolving, this field appears to be heading in the direction of using starting materials with a significantly lower degree of prefunctionalization in addition to less expensive and abundant metal catalysts.

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“…273 The reaction uses a mixture of Selectfluor and NaF, but isotope labeling studies using 18 F have demonstrated that the fluorine atom in the product originates in the electrophilic fluorine reagent (Scheme 92).…”

Section: Scheme 91mentioning

confidence: 99%