46883-44-7Relevant academic research and scientific papers
Aerobic cross-dehydrogenative couplings of N-heteroarenes with toluene derivatives at room temperature
Chen, Yufeng,Deng, Guo-Jun,Huang, Huawen,Sun, Zhaozhao,Wang, Qiao-Lin
supporting information, p. 7790 - 7795 (2021/10/12)
A set of mild aerobic cross-dehydrogenative couplings of N-heteroarenes with the benzylic C(sp3)-H bond has been achieved by using visible-light-induced photocatalysis. This approach was found to provide a sustainable alternative to Minisci benzylation reactions using readily accessible toluene derivatives as benzylating agents. The unique combination of photocatalysis, bromo radical mediation, and aerobic oxidation proved to be the key for the success of the transformation. Mechanistic studies revealed the feasibility of both oxidative and reductive quenching of the excited photocatalyst in the initial step.
Visible-light-induced C(sp3)-H oxidative arylation with heteroarenes
Liang, Xing-An,Niu, Linbin,Wang, Shengchun,Liu, Jiamei,Lei, Aiwen
supporting information, p. 2441 - 2444 (2019/03/26)
Considering the ubiquitous C(sp3)-H and the important value of alkylated heteroarenes, developing a universal method for C(sp3)-H arylation with heteroarenes is significant. Herein, we proposed a method where Selectfluor can promote
Oxidant-Triggered C1-Benzylation of Isoquinoline by Iodine-Catalyzed Cross-Dehydrogenative-Coupling with Methylarenes
Shi, Xin,Zhang, Feng,Luo, Wen-Kun,Yang, Luo
supporting information, p. 494 - 498 (2017/02/24)
A practical iodine-catalyzed oxidative functionalization of isoquinolines with methylarenes is developed, which can be triggered by the selected oxidants to produce C1- or N-benzyl-substituted products selectively. This method utilizes readily available isoquinolines and methylarenes as starting materials and proceeds under metal-free conditions with broad substrate scope with respect to methylarenes, avoiding the usage of expensive metal catalysts and generation of halide and metal wastes.
Ruthenium-Mediated Dual Catalytic Reactions of Isoquinoline via C?H Activation and Dearomatization for Isoquinolone
Wang, Ting-Hsuan,Lee, Wei-Chih,Ong, Tiow-Gan
supporting information, p. 2751 - 2758 (2016/09/13)
We have unraveled the ruthenium-promoted prototype reaction based on C(sp2)?C(sp3) bond formation through the reigoselective C?H activation of isoquinoline and pyridine derivatives with various alkyl halides, leading to 1-substituted isoquinoline products in good yield. This C?H catalytic reaction did not rely on chelation assistance of the directing group of the substrates. The dimer [RuCl2(p-cymene)]2in combination with an N-heterocyclic carbene ligand, adamantanecarboxylic acid and K2CO3base in N-methyl-2-pyrrolidone solution at 150 °C are the best conditions. Simultaneously, we are also able to chemically tune the reaction mode to dearomatization by adding water, leading to isoquinolone products. This reaction methodology is not suitable for other nitrogen-containing heteroarenes such as pyridazines and pyrimidines. (Figure presented.).
C1-Benzyl and benzoyl isoquinoline synthesis through direct oxidative cross-dehydrogenative coupling with methyl arenes
Wan, Miao,Lou, Hongxiang,Liu, Lei
supporting information, p. 13953 - 13956 (2015/09/07)
An oxidative cross-dehydrogenative coupling (CDC) of isoquinolines with methyl arenes has been developed, allowing for the facile synthesis of a broad range of structurally diverse C1-benzyl and -benzoyl isoquinolines. The direct use of readily available methyl arenes as coupling partners avoids unproductive steps for preactivating the functional group installation, and is therefore attractive. The method exhibits excellent chemoselectivity, affording exclusive benzylated products in the presence of DTBP and a catalytic amount of Y(OTf)3, and yielding benzoylated ones with TBHP and a catalytic amount of MnO2.
WITTIG-HORNER REACTION OF A PHOSPHONATE OF REISSERT ANALOGUE A NEW METHOD FOR INTRODUCTION OF ALKYL GROUPS INTO ISOQUINOLINE
Akiba, Kin-ya,Negishi, Yoshio,Kurumaya, Katsuyuki,Ueyama, Noboru,Inamoto, Naoki
, p. 4977 - 4980 (2007/10/02)
Dimethyl 2-isopropoxycarbonyl-1,2-dihydroisoquinoline-1-phosphonate (1) was prepared from isoquinoline, isopropyl chloroformate, and trimethyl phosphite.Wittig-Horner reaction of 1 with various aldehydes afforded the corresponding exo-methylene compounds,
