Direct Access to α,α‐Difluoroacylated Arenes by Palladium‐Catalyzed Carbonylation of (Hetero)Aryl Boronic Acid Derivatives

Andersen, T.; Frederiksen, Mette W.; Domino, Katrine; Skrydstrup, Troels

doi:10.1002/ange.201604152

Cited by 17 publications

(1 citation statement)

References 43 publications

(4 reference statements)

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“…5 These carbonylative reactions reportedly involve the formation of open-shell species after bromide abstraction from the α-bromo-α,α-difluoroacetamides. 5a 6…”

Section: Table 1 Optimization Of the Nickel-catalyzed C...mentioning

confidence: 99%

Nickel-Catalyzed Carbonylative Coupling of Alkylzinc Reagents and α-Bromo-α,α-difluoroacetamides

Corneliussen¹,

Grove²,

Schøler³

et al. 2023

Synlett

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Herein, we report a nickel catalyzed carbonylative cross coupling of alkyl zinc reagents and α,α-difluorobromoaceamides to obtain α,α,-difluoro-α-ketoamides in moderate to good yields. The reaction is catalyzed by a bench stable nickel(II) pincer complex, in contrast to other reports based on palladium catalysts. The carbonylative reaction is performed in a two-chamber system (COware®), in which carbon monoxide (CO) is generated ex situ from the solid precursor, SilaCOgen, and consumed in the adjacent chamber. The reaction operates at low temperatures using near stoichiometric amounts of CO, and isotopically labeled products are effortlessly accessed as demonstrated using 13C-labeled SilaCOgen.

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“…5 These carbonylative reactions reportedly involve the formation of open-shell species after bromide abstraction from the α-bromo-α,α-difluoroacetamides. 5a 6…”

Section: Table 1 Optimization Of the Nickel-catalyzed C...mentioning

confidence: 99%

Nickel-Catalyzed Carbonylative Coupling of Alkylzinc Reagents and α-Bromo-α,α-difluoroacetamides

Corneliussen¹,

Grove²,

Schøler³

et al. 2023

Synlett

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α,α‐Difluoro‐α‐(trimethylsilyl)acetamides as Versatile Reagents for the Preparation of Difluorinated Aldol and Mannich Adducts

et al. 2017

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Thev ery efficient addition of a,a-difluoroa-(trimethylsilyl)acetamides to aldehydes,k etones and N-(tert-butanesulfinyl)imines is described. The reactioni sp romoted by ac atalytic amount of tetran-butylammonium diphenyltrifluorosilicate (TBAT) and high yields,a sw ell as very high stereoselectivities in the case of N-(tert-butanesulfinyl)imines,a re achieved. Thes ynthetic potentialo ft his method is il-lustrated by the conversion of the resulting products to b-hydroxy ketones,d iols and b-amino alcohols by addition of various Grignard reagents or reduction of the amide moiety.

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Alternative Palladium‐Catalyzed Vinylic C−H Difluoroalkylation of Ketene Dithioacetals Using Bromodifluoroacetate Derivatives

et al. 2018

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A palladium‐catalyzed cross‐coupling of α‐oxo ketene dithioacetals and bromodifluoroacetate derivatives has been developed for the synthesis of a class of CF2‐containing tetra‐substituted olefins, which has potential to extend to drug design and material application. The process is proposed to involve two single electron transfer processes accompanied by an alternative loop from palladium(0) to palladium(I), likely due to unique structural properties of ketene dithioacetals with β,β‐dialkylthiol substituents on the olefin double bond.magnified image

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Direct Access to α,α‐Difluoroacylated Arenes by Palladium‐Catalyzed Carbonylation of (Hetero)Aryl Boronic Acid Derivatives

Cited by 17 publications

References 43 publications

Nickel-Catalyzed Carbonylative Coupling of Alkylzinc Reagents and α-Bromo-α,α-difluoroacetamides

Nickel-Catalyzed Carbonylative Coupling of Alkylzinc Reagents and α-Bromo-α,α-difluoroacetamides

α,α‐Difluoro‐α‐(trimethylsilyl)acetamides as Versatile Reagents for the Preparation of Difluorinated Aldol and Mannich Adducts

Alternative Palladium‐Catalyzed Vinylic C−H Difluoroalkylation of Ketene Dithioacetals Using Bromodifluoroacetate Derivatives

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