A General Method for the Synthesis of Unsymmetrically Substituted Ureas via Palladium-Catalyzed Amidation

Kotecki, Brian J.; Fernando, Dilinie P.; Haight, Anthony R.; Lukin, K. A.

doi:10.1021/ol802931m

Cited by 78 publications

(48 citation statements)

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“…38 Researchers at Abbot reported that palladium complexes of BippyPhos catalyze the N -arylation of ureas. 39 Finally, Beller has shown that the combination of palladium and AdBippyPhos catalyzes the etherification of aryl halides with primary alcohols. 40 …”

Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed Arylation of Fluoroalkylamines

2015

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We report the synthesis of fluorinated anilines by palladium-catalyzed coupling of fluoroalkylamines with aryl bromides and aryl chlorides. The products of these reactions are valuable because anilines typically require the presence of an electron-withdrawing substituent on nitrogen to suppress aerobic or metabolic oxidation, and the fluoroalkyl groups have steric properties and polarity distinct from those of more common electron-withdrawing amide and sulfonamide units. The fluoroalkylaniline products are unstable under typical conditions for C–N coupling reactions (heat and strong base). However, the reactions conducted with the weaker base KOPh, which has rarely been used in cross-coupling to form C–N bonds, occurred in high yield in the presence of a catalyst derived from commercially available AdBippyPhos and [Pd(allyl)Cl]2. Under these conditions, the reactions occur with low catalyst loadings (<0.50 mol % for most substrates) and tolerate the presence of various functional groups that react with the strong bases that are typically used in Pd-catalyzed C–N cross-coupling reactions of aryl halides. The resting state of the catalyst is the phenoxide complex, (BippyPhosPd(Ar)OPh); due to the electron-withdrawing property of the fluoroalkyl substituent, the turnover-limiting step of the reaction is reductive elimination to form the C–N bond.

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Section: Resultsmentioning

confidence: 99%

Palladium-Catalyzed Arylation of Fluoroalkylamines

2015

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“…[ [37][38][39][40] In 2013, Kumar et al reported a copper ferrite catalyst system for the same reaction. [41] These copper ferrite nanoparticles were previously used by Sun et al in the CÀO bond formation reaction.…”

Section: Introductionmentioning

confidence: 99%

CN Bond Formation Using Highly Effective and Reusable Nickel Ferrite Nanoparticles in Water

et al. 2014

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The inside cover picture, by Kerr and co‐workers, depicts a series of robust, yet highly active Ir(I) complexes bearing specifically encumbered N‐heterocyclic carbene and phosphine ligands. These complexes are extremely effective in hydrogen isotope exchange processes (with D or T), with low catalyst loadings, good levels of selectivity, and broad directing group applicability. The labelling of several complex drug molecules further highlights the catalysts utility. Mechanistic insight into the operation of these catalysts has also been provided by a combination of NMR and theoretical DFT studies. Details of this work can be found in the full paper on .

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“…Nevertheless, a general method for the synthesis of unsymmetrical urea derivatives via Pd-catalyzed C-N single-bond formation was developed by Kotecki et al [127]. A bipyrazolederived electron-rich monodentate phosphine 61 was employed in the arylation of N-phenyl-and N-cyclohexyl-substituted urea with aryl bromides and chlorides (Scheme 13.81).…”

Section: Arylation Of Amide Urethane Urea and Sulfonic Acid Amide mentioning

confidence: 99%

Palladium‐Catalyzed Aromatic Carbon–Nitrogen Bond Formation

Paradies

2013

Metal‐Catalyzed Cross‐Coupling Reactions and More

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A General Method for the Synthesis of Unsymmetrically Substituted Ureas via Palladium-Catalyzed Amidation

Cited by 78 publications

References 16 publications

Palladium-Catalyzed Arylation of Fluoroalkylamines

Palladium-Catalyzed Arylation of Fluoroalkylamines

CN Bond Formation Using Highly Effective and Reusable Nickel Ferrite Nanoparticles in Water

Palladium‐Catalyzed Aromatic Carbon–Nitrogen Bond Formation

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