In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides

Milner, Phillip J.; Yang, Yang; Buchwald, Stephen L.

doi:10.1021/acs.organomet.5b00631

Cited by 48 publications

(34 citation statements)

References 45 publications

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“…In many instances, the rate-determining step of Pd-catalyzed coupling reactions with five-membered heteroaryl halides is reductive elimination. 448 , 472 , 473 Moreover, these substrates have great structural diversity. Five-membered heterocycles can have one or more heteroatoms (O, S, and N), be benzo-fused, or contain free NH groups.…”

Section: Five-membered Heteroaryl Halidesmentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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Pd-catalyzed cross-coupling reactions that form C–N bonds have become useful methods to synthesize anilines and aniline derivatives, an important class of compounds throughout chemical research. A key factor in the widespread adoption of these methods has been the continued development of reliable and versatile catalysts that function under operationally simple, user-friendly conditions. This review provides an overview of Pd-catalyzed N-arylation reactions found in both basic and applied chemical research from 2008 to the present. Selected examples of C–N cross-coupling reactions between nine classes of nitrogen-based coupling partners and (pseudo)aryl halides are described for the synthesis of heterocycles, medicinally relevant compounds, natural products, organic materials, and catalysts.

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Section: Five-membered Heteroaryl Halidesmentioning

confidence: 99%

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

2016

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“…3‐Bromo‐2‐(2‐bromophenyl)thiophene : The title compound (8.5 g, 26.7 mmol, 87 %) was prepared by a modified procedure reported for the synthesis of 3‐bromo‐2‐phenylthiophene by using 1‐bromo‐2‐iodobenzene (7.9 mL, 61.4 mmol) in place of phenylboronic acid. 1 H NMR (400 MHz, CDCl 3 , 298 K): δ =7.06 (d, J =7.8 Hz, 1 H; thienyl), 7.26–7.27 (m, 1 H; phenyl), 7.36–7.39 (m, 3 H; phenyl), 7.68 ppm (d, J =7.8 Hz, 1 H; thienyl); m / z (EI + ): 317.9 [ M ] + .…”

Section: Methodsmentioning

confidence: 99%

Supramolecular Assembly of Phosphole Oxide Based Alkynylplatinum(II) 2,6‐Bis(N‐alkylbenzimidazol‐2’‐yl)pyridine Complexes—An Interplay of Hydrophobicity and Aromatic π‐Surfaces

Cheung

Hong

Yam

2017

Chemistry A European J

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A new class of phosphole oxide based alkynylplatinum(II) 2,6-bis(N-alkylbenzimidazol-2'-yl)pyridine (bzimpy) complexes were synthesized and characterized. Their self-assembly was driven by hydrophobic-hydrophobic and π-π stacking interactions. The self-assembly properties were also investigated by UV/Vis absorption spectroscopy, which revealed that the alkyl-chain length of the bzimpy moiety and the π-surface area of the alkynyl ligand have significant influence on the overall self-assembly process. The alkyl-chain length also affected the morphological structures of the aggregates, which were studied by transmission electron microscopy and scanning electron microscopy.

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“…188 This study arose in part from the difficulty in accessing fivemembered aryl fluorides from the corresponding aryl bromides under previously established reaction conditions. 147…”

Section: Carbon−halogen Reductive Elimination From Pd(ii) 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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In-Depth Assessment of the Palladium-Catalyzed Fluorination of Five-Membered Heteroaryl Bromides

Cited by 48 publications

References 45 publications

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Applications of Palladium-Catalyzed C–N Cross-Coupling Reactions

Supramolecular Assembly of Phosphole Oxide Based Alkynylplatinum(II) 2,6‐Bis(N‐alkylbenzimidazol‐2’‐yl)pyridine Complexes—An Interplay of Hydrophobicity and Aromatic π‐Surfaces

Modern Transition-Metal-Catalyzed Carbon–Halogen Bond Formation

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