Pd‐Catalyzed Coupling Cyclization of δ, ϵ‐Alkenyl Oxime toward Access to 1, 2‐Oxezapines. Issue 1 (28th December 2022)

• Record Type: Journal Article
• Authors: Zhao, Chuang; Dong, Ah‐Ying; Ju, Dongyan; Huang, Jianhong; Jia, Ran; Liu, Yu; Zhao, Jinbo
• Is Part Of: Asian journal of organic chemistry. Volume 12:Issue 1(2023)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-28
• Subjects: Cyclization -- palladium catalysis -- oxezapine -- oxime; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.202200635
• Languages: English
• ISSNs: 2193-5807

Abstract

Abstract: The Pd‐catalyzed coupling cyclization of δ, ϵ‐alkenyl oxime with (hetero)aryl and halides is presented, which affords seven membered N, O ‐heterocycle, tetrahydro‐1, 2‐oxezapines, in moderate to good yields. DFT calculation favors an outer‐sphere anti ‐oxypalladation pathway and provides key insights on the reaction mechanism. The reaction represents an unprecedented example of seven‐membered ring formation by heterocyclization. Abstract : The Pd‐catalyzed coupling cyclization of δ, ϵ‐alkenyl oxime with aryl halides provided carbon‐tethered‐ and benzo‐1, 2‐oxezapines in moderate to good yields. DFT calculation suggests that the reaction might proceed via a trans ‐oxypalladation process, in contrast to the analogous 5‐ and 6‐membered annulation.