Copper‐Catalyzed C(sp3)‐Amination of Ketone‐Derived Dihydroquinazolinones by Aromatization‐Driven C−C Bond Scission

• Published in: Angewandte Chemie International Edition Vol. 62; no. 8; pp. e202217386 - n/a
• Main Authors: Lv, Xin‐Yang, Abrams, Roman, Martin, Ruben
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 13.02.2023; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Amination; Chemistry; Chemistry, Multidisciplinary; Cleavage; Copper; C−C Functionalization; Intermediates; Ketones; Physical Sciences; Proaromaticity; Science & Technology; OXIDATION; ACTIVATION; Ketones; AMIDATION; CARBON-CARBON BONDS; Amination; AMINES; COUPLINGS; Copper; SECONDARY ALKYL-HALIDES; C-C Functionalization; Proaromaticity; IMIDATION; C−C Functionalization
• ISSN: 1433-7851; 1521-3773; 1521-3773
• DOI: 10.1002/anie.202217386

Herein, we describe the development of a copper‐catalyzed C(sp3)‐amination of proaromatic dihydroquinazolinones derived from ketones. The reaction is enabled by the intermediacy of open‐shell species arising from homolytic C−C bond‐cleavage driven by aromatization. The protocol is characterized by its operational simplicity and generality, including chemical diversification of advanced intermediates. Herein, we describe the development of a copper‐catalyzed C(sp3)‐amination of proaromatic dihydroquinazolinones derived from ketone building blocks. The reaction is enabled by the intermediacy of open‐shell species arising from homolytic C−C bond‐cleavage driven by aromatization. The protocol is characterized by its operational simplicity and generality, including chemical diversification of advanced intermediates.