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Article Dans Une Revue Organic Letters Année : 2023

Copper-Catalyzed, Ligand-Controlled N(sp3)- or N(sp)-Selective Arylation of Cyanamides

Résumé

Cyanamides possess both nucleophilic and electrophilic centers, and their arylation reactions are known to proceed at N(sp3) and C(sp) sites, leading to N-aryl cyanamides or amidines. N(sp) selectivity has also been reported only in the presence of amines, thus leading to guanidines. Herein, we report a general copper-catalyzed ligand-controlled Chan-Lam-Evans arylation of cyanamides proceeding regioselectively at the N(sp3) or N(sp) atoms and leading to either N-aryl cyanamides or dissymmetric carbodiimides. The nature of the ligand, either a bipyridine or a diamine, controls the product distribution and thus offers a divergent entry to useful building blocks from readily available cyanamides.
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Dates et versions

hal-04264724 , version 1 (31-10-2023)

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Jiaqi Fang, Oumaïma Bekkouch, Guilhem Zeiser, Yurii Zubchuk, Vincent Bizet, et al.. Copper-Catalyzed, Ligand-Controlled N(sp3)- or N(sp)-Selective Arylation of Cyanamides. Organic Letters, 2023, 25 (34), pp.6446-6451. ⟨10.1021/acs.orglett.3c02622⟩. ⟨hal-04264724⟩
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