80965-23-7Relevant academic research and scientific papers
Access to Branched Allylarenes via Rhodium(III)-Catalyzed C-H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate
Zhang, Shang-Shi,Zheng, Yi-Chuan,Zhang, Zi-Wu,Chen, Shao-Yong,Xie, Hui,Shu, Bing,Song, Jia-Lin,Liu, Yan-Zhi,Zeng, Yao-Fu,Zhang, Luyong
supporting information, p. 5719 - 5723 (2021/08/16)
A rhodium(III)-catalyzed C-H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.
Direct Oxygenation of C-H Bonds through Photoredox and Palladium Catalysis
Paul, Amrita,Shah, Sk. Sheriff,Shee, Maniklal,Singh, Amit Kumar,Singh, N. D. Pradeep
, p. 3426 - 3439 (2020/03/23)
This report presents the oxygenation of C-H bonds via the merger of photocatalysis and Pd catalysis. Herein, we describe the utilization of a photocatalyst to oxidize an organopalladium(II) intermediate to high-valent PdIII or PdIV intermediates, which promotes the formation of C-O bonds. The demonstrated method works efficiently with various directing groups, such as oxime ether and benzothiazole. The applicability of this direct C-O bond formation method is shown by synthesizing several metal complexes of 2-(benzo[d]thiazol-2-yl)phenol that can be used in organic light-emitting diodes and pharmaceuticals.
Nitrate promoted mild and versatile Pd-catalysed C(sp2)-H oxidation with carboxylic acids
Hao, Hong-Yan,He, Yu-Ting,Lou, Shao-Jie,Luo, Gen,Mao, Yang-Jie,Xiong, Xue,Xu, Dan-Qian,Xu, Zhen-Yuan
supporting information, p. 6732 - 6737 (2020/09/21)
A nitrate-promoted Pd-catalysed mild cross-dehydrogenative C(sp2)-H bond oxidation of oximes or azobenzenes with diverse carboxylic acids has been developed. In contrast to the previous catalytic systems, this protocol features mild conditions (close to room temperature for most cases) and a broad substrate scope (up to 64 examples), thus constituting a versatile method to directly prepare diverse O-aryl esters. Moreover, the superiority of the nitrate additive in this mild transformation was further determined by experimental and computational evidence.
Catalyst-Controlled [3 + 2] and [4 + 2] Annulations of Oximes with Propargyl Alcohols: Divergent Access to Indenamines and Isoquinolines
Gong, Wanchun,Zhou, Zhi,Shi, Jingjing,Wu, Bo,Huang, Biyun,Yi, Wei
supporting information, p. 182 - 185 (2018/01/17)
Rhodium(III)- and iridium(III)-catalyzed C-H activation of oximes and coupling with propargyl alcohols is discussed. Depending on the catalyst, the reaction pathway switched between [3 + 2] and [4 + 2] annulations, thus giving divergent access to indenami
Palladium-Catalyzed C(sp2)-H Acetoxylation via Electrochemical Oxidation
Li, Yi-Qian,Yang, Qi-Liang,Fang, Ping,Mei, Tian-Sheng,Zhang, Dayong
supporting information, p. 2905 - 2908 (2017/06/07)
Palladium-catalyzed arene C(sp2)-H acetoxylation has emerged as a powerful tool to construct a carbon-oxygen (C-O) bond. However, the requirement of stoichiometric chemical oxidants for this transformation possesses a significant disadvantage.
Synthesis of 2-fluorocholine aryl carbonyl compounds
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Paragraph 0060, (2017/02/09)
The invention provides a method for synthesizing 2-fluoroarylcarbonyl compounds, which comprises the following steps: converting arylcarbonyl compounds into corresponding carbonyl oxime ether compounds, mildly implementing aryl hydrocarbon chain direct fluoridation of high-selectivity oximido substituent group ortho-position in the presence of a palladium catalyst, a fluoridation reagent and additives, and finally, rehydrolyzing oxime ethers under the action of acid to obtain the 2-fluoroarylcarbonyl compounds. The fluoridation method has the advantages of mild reaction conditions, high substrate adaptability, high fluoridation selectivity and the like, is simple to operate, and has higher application research value.
NHPI and palladium cocatalyzed aerobic oxidative acylation of arenes through a radical process
Liang, Yu-Feng,Wang, Xiaoyang,Tang, Conghui,Shen, Tao,Liu, Jianzhong,Jiao, Ning
supporting information, p. 1416 - 1419 (2016/01/25)
The NHPI and palladium cocatalyzed radical oxidative acylation of arenes with aldehydes and alcohols as acyl equivalents via selective C-H functionalization has been described. Molecular oxygen, the most environmentally friendly oxidant, was used as the terminal oxidant in this catalytic cycle.
Direct C-H amination of arenes with alkyl azides under rhodium catalysis
Shin, Kwangmin,Baek, Yunjung,Chang, Sukbok
supporting information, p. 8031 - 8036 (2013/08/23)
New horizons in the utility of azides: The rhodium-catalyzed intermolecular direct C-H amination of arenes with alkyl azides provides a convenient route to N-alkyl anilines (see scheme; DG=directing group). Alkyl azides with a wide range of functional groups reacted readily with various substrates, including benzamides, aromatic ketones, and flavones. Copyright
[Cp*RhCl2]2-catalyzed ortho-C-H bond amination of acetophenone o-methyloximes with primary N-chloroalkylamines: Convenient synthesis of N-alkyl-2-acylanilines
Ng, Ka-Ho,Zhou, Zhongyuan,Yu, Wing-Yiu
supporting information, p. 7031 - 7033 (2013/09/02)
Rh(iii)-catalyzed aromatic C-H amination of acetophenone o-methyloximes with primary N-chloroalkylamines was developed, and the arylamine products were obtained in up to 92% yield. The reaction probably involves rate-limiting electrophilic C-H bond cleavage (kH/kD = 2).
Rhodium-catalyzed directed C-H cyanation of arenes with N-cyano-N-phenyl-p-toluenesulfonamide
Gong, Tian-Jun,Xiao, Bin,Cheng, Wan-Min,Su, Wei,Xu, Jun,Liu, Zhao-Jing,Liu, Lei,Fu, Yao
supporting information, p. 10630 - 10633 (2013/08/23)
A Rh-catalyzed directed C-H cyanation reaction was developed for the first time as a practical method for the synthesis of aromatic nitriles. N-Cyano-N-phenyl-p-toluenesulfonamide, a user-friendly cyanation reagent, was used in the transformation. Many different directing groups can be used in this C-H cyanation process, and the reaction tolerates a variety of synthetically important functional groups.
