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

par Fang, Jiaqi ;Bekkouch, Oumaïma;Zeiser, Guilhem;Zubchuk, Yurii;Bizet, Vincent;Blanchard, Nicolas;Evano, Gwilherm
Référence Organic letters, 25, page (6446-6451)
Publication Publié, 2023-08-21

Article révisé par les pairs

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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 to 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.