408368-26-3Relevant academic research and scientific papers
Nickel-Catalyzed Suzuki-Miyaura Cross-Coupling Involving C?O Bond Activation
Morishige, Aoi,Iyori, Yasuaki,Chatani, Naoto
, (2021/07/17)
An efficient Suzuki-Miyaura cross-coupling reaction of ortho-phenoxy-substituted aromatic amides with aryl boronates is described. The use of LiOtBu is crucial for the success of the reaction. An amidate anion, which is formed through deprotonation of the amide NH bond by LiOtBu, functions as a directing group to activate a C?O bond.
Nickel-Mediated Cross-Coupling of Boronic Acids and Phthalimides for the Synthesis of Ortho-Substituted Benzamides
Ahlgrim, Grace C.,Deglopper, Kimberly S.,Dennis, Joseph M.,Heyboer, Ethan M.,Johnson, Jeffrey B.,Johnson, Rebecca L.,Kwiatkowski, Megan R.,Pankratz, Trey C.,Yoder, Mason C.
, p. 3757 - 3765 (2020/03/23)
The decarbonylative coupling of phthalimides with aryl boronic acids provides ready access to a broad range of ortho-substituted benzamides. This nickel-mediated methodology extends reactivity from previously described air-sensitive diorganozinc reagents of limited availability to easily handled and widely commercially available boronic acids. The decarbonylative coupling is tolerant of a broad range of functional groups and demonstrates little sensitivity to steric factors on either of the coupling partners.
Transition-Metal-Free Synthesis of Phenanthridinones through Visible-Light-Driven Oxidative C–H Amidation
Usami, Kaoru,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
, p. 1496 - 1504 (2019/06/27)
The treatment of N-aryl biphenylcarboxamide, 1-chloroanthraquinone (1-Cl-AQN) catalyst, and K2CO3 in CHCl3 under visible light irradiation affords phenanthridinone via radical cyclization. This reaction proceeds under transition-metal-free condition, room temperature, and direct C–H amidation. Mechanistic studies indicate that amidyl radical generation proceeds by visible light induced proton coupled electron transfer (PCET) from N–H bond of the amide.
Nickel-mediated decarbonylative cross-coupling of phthalimides with in situ generated diorganozinc reagents
Havlik, Sarah E.,Simmons, Jessica M.,Winton, Valerie J.,Johnson, Jeffrey B.
experimental part, p. 3588 - 3593 (2011/06/26)
The nickel-mediated cross-coupling of phthalimides with diorganozinc reagents proceeds via a decarbonylative process to produce ortho-substituted benzamides in high yields. In addition to tolerating diverse phthalimide functionality, including alkyl, aryl
