Copper-Catalyzed, Ligand-Controlled N(sp3)- or N(sp)-Selective Arylation of Cyanamides
In: ISSN: 1523-7060, 2023
Online
academicJournal
Zugriff:
International audience ; 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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Copper-Catalyzed, Ligand-Controlled N(sp3)- or N(sp)-Selective Arylation of Cyanamides
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Autor/in / Beteiligte Person: | Fang, Jiaqi ; Bekkouch, Oumaïma ; Zeiser, Guilhem ; Zubchuk, Yurii ; Bizet, Vincent ; Blanchard, Nicolas ; Evano, Gwilherm ; Laboratoire d'innovation moléculaire et applications (LIMA) ; Université de Strasbourg (UNISTRA)-Université de Haute-Alsace (UHA) Mulhouse - Colmar (Université de Haute-Alsace (UHA))-Institut de Chimie - CNRS Chimie (INC-CNRS)-Centre National de la Recherche Scientifique (CNRS) ; Université libre de Bruxelles (ULB) |
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Zeitschrift: | ISSN: 1523-7060, 2023 |
Veröffentlichung: | HAL CCSD ; American Chemical Society, 2023 |
Medientyp: | academicJournal |
DOI: | 10.1021/acs.orglett.3c02622 |
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