Amination and Formation of sp2 C-N Bonds by Georgia S. Lemen, John P. Wolfe (auth.), Marc Taillefer,

By Georgia S. Lemen, John P. Wolfe (auth.), Marc Taillefer, Dawei Ma (eds.)

Palladium-Catalyzed sp2C–N Bond Forming Reactions: contemporary advancements and functions. Metal-catalyzed C(sp2)-N bond formation.- contemporary advancements in Recyclable Copper Catalyst platforms for C−N Bond Forming Cross-Coupling Reactions utilizing Aryl Halides and Arylboronic Acids. meeting of N-containing heterocycles through Pd and Cu-catalyzed C-N bond formation reactions. Copper-Catalyzed C(aryl)-N Bond Formation.

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For example, Bra¨se has developed a diastereoselective coupling of enantiopure amine 24 with (Æ)-23 (2 equiv) that affords 25 in 70% yield and 98% de (Eq. 44) [248]. 42 equiv of an aryl bromide demonstrated that up to 80% ee could be obtained for certain combinations of substrates when (R)-Tol-BINAP was employed as ligand [249]. However, most reactions proceeded with considerably lower selectivity (5–72% ee). Kitagawa and Taguchi have developed a new approach to the synthesis of axially chiral N-(p-nitrophenyl)anilides.

Bringmann and coworkers utilized the coupling of t-butylcarbamate with a bromonaphthalene derivative as part of a convergent synthesis of Ancisheynine (Scheme 7) [323]. Ganton and Kerr have demonstrated that the CPI subunit of CC-1065, which has shown antitumor activity, can be synthesized using an intramolecular amidation as one of the key transformations (Eq. 61) [324]. 5 mol %) O MeO NH N+ – OTf OMe OMe OMe OMe OMe Scheme 7 Palladium-Catalyzed N-Arylation in the Synthesis of Ancisheynine MOMO H N OTf N Ts MOMO Bz Pd2(dba)3 (10 mol %) Xantphos (20 mol %) Cs2CO3, dioxane 88% OBn N N Ts Bz ð61Þ OBn Alkenyl halides and triflates have also been employed in the generation of biologically active compounds and natural products.

The preparation of 2-quinolones has been achieved via a cascade intermolecular Heck arylation/intramolecular N-arylation sequence between o-bromocinnamide and aryl iodides [294]. The synthesis of quinazolinediones via a tandem acylation/Pd-catalyzed N-arylation reaction between o-halobenzoates and monoalkylureas has also been described [295]. An interesting cascade reaction involving Pd-catalyzed C–C and C–N bond formation effects the conversion of 2-bromobenzamide derivatives (2 equiv) to phenanthridones (Eq.

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