1286261-77-5Relevant 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.
Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides
Samanta, Partha Kumar,Biswas, Papu
, p. 3968 - 3976 (2019/03/26)
The Pd(OAc)2 catalyzed cross-coupling of N-substituted phthalimides with aryl halide provides a single step direct access of a wide range of synthetically appealing ortho-substituted biarylamides in high yields through unique carbonyl (CO) replacement. The reaction proceeds through a ligand-free condition and is well tolerant to the diverse functionality of both imide and halide units. The reaction negates any requirement of organometallic reagent and needs a shorter reaction time and comparatively lower temperature as required for previously reported decarbonylative processes.
Nickel-Catalyzed Denitrogenative Cross-Coupling Reaction of 1,2,3-Benzotriazin-4(3 H)-ones with Organoboronic Acids: An Easy Access to Ortho-Arylated and Alkenylated Benzamides
Hari Balakrishnan, Madasamy,Sathriyan, Kotturaja,Mannathan, Subramaniyan
supporting information, p. 3815 - 3818 (2018/07/25)
A novel nickel-catalyzed approach to synthesize ortho-arylated and alkenylated benzamides in good to high yields via a denitrogenative cross-coupling reaction of 1,2,3-benzotriazin-4(3H)-ones with organoboronic acids is described. The reaction proceeds th
Iron-catalyzed oxidative biaryl cross-couplings via mixed diaryl titanates: Significant influence of the order of combining aryl Grignard reagents with titanate
Liu, Kun Ming,Wei, Juan,Duan, Xin Fang
supporting information, p. 4656 - 4658 (2015/05/27)
The mixed diaryl titanates were used for the first time to modify the reactivity of two aryl Grignard reagents. Two titanate intermediates, Ar[Ar′Ti(OR)3]MgX and Ar′[ArTi(OR)3]MgX, formed via alternating the sequence of combining Grignard reagents with ClTi(OR)3 showed a significant reactivity difference. Taking advantage of such different reactivity, two highly structurally similar aryl groups could be facilely assembled through iron-catalyzed oxidative cross-couplings using oxygen as the oxidant. This journal is
Palladium(II)-catalyzed auxiliary-directed C-H activation for the regioselective ortho arylation of N -(2-benzoylphenyl)benzamides
Subba Reddy, Basi V.,Revathi,Reddy, A. Srinivas,Yadav, Jhillu S.
body text, p. 2374 - 2378 (2011/10/13)
A highly regioselective ortho arylation of N-(2-benzoylphenyl)benzamides has been achieved with aryl iodides in the presence of 10 mol% Pd(OAc)and a stoichiometric amount of AgOAc under solvent-free conditions via C-H activation to produce the correspondi
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
