1496-76-0Relevant articles and documents
Selective N1-Acylation of Indazoles with Acid Anhydrides Using an Electrochemical Approach
DIssanayake, D.M.M. Mevan,Vannucci, Aaron K.
, p. 457 - 460 (2019)
An electrochemical synthesis method for the selective N1-acylation of indazoles has been developed. This "anion pool" approach electrochemically reduces indazole molecules generating indazole anions and H2. Acid anhydrides are then introduced to the solution resulting in selective acylation of the N1-position of the indazoles. This procedure can also be applied to the acylation of benzimidazoles and indoles. The reaction can also be performed using a 9 V battery without loss of reaction efficiency.
An effective C-C double bond formation via Cu(I)-catalyzed dehydrogenation
Ramirez, Thomas A.,Zhao, Baoguo,Shi, Yian
, p. 1822 - 1825 (2010)
A dehydrogenation method using Cu(I) and either N,N-di-tert-butylthiadiaziridine 1,1-dioxide or N,N-di-tert-butyldiaziridinone is reported. The dehydrogenation allows a facile introduction of C-C double bond(s) into various carbocycles and heterocycles such as oxazolines and thiazolines.
Na 2 CO 3-Catalyzed N-Acylation of Indoles with Alkenyl Carboxylates
Zhou, Xiao-Yu,Chen, Xia
, p. 516 - 521 (2019)
The N-acylation of indoles has been accomplished via inorganic base catalysis. It provided an efficient and simple catalysis system for the preparation of N-acylindoles with alkenyl carboxylates as acylating agents. A broad variety of indoles undergo the smooth N-acylation using Na 2 CO 3 as catalyst in MeCN at 120? °C to give the corresponding N-acylindoles in good to excellent yields.
Trifluoromethylselenolation andN-acylation of indoles with [Me4N][SeCF3]
Dong, Tao,Tan, Kai-Li,Wang, Hao-Nan,Zhang, Cheng-Pan
, p. 5368 - 5376 (2021)
An efficient method for oxidative trifluoromethylselenolation/N-acylation of indoles with excess [Me4N][SeCF3] in the presence of acyl peroxides and their derivatives is described. The reaction is easy to handle, proceeds smoothly at room temperature under metal-free conditions, and shows advantages such as good functional group tolerance, excellent regioselectivity, and compatibility of a number of substrates, producing 1-acyl and 3-trifluoromethylselanyl substituted indoles in good yields. Acyl peroxides and peroxycarboxylic acid behave as both oxidants and acyl sources in the transformation. This one-pot procedure provides a convenient access to a new class of indole derivatives, representing the first trifluoromethylselanyl bifunctionalization of indoles with the nucleophilic [Me4N][SeCF3] reagent.
Photoredox Catalysis Induced Bisindolylation of Ethers/Alcohols via Sequential C-H and C-O Bond Cleavage
Ye, Lu,Cai, Sai-Hu,Wang, Ding-Xing,Wang, Yi-Qiu,Lai, Lin-Jie,Feng, Chao,Loh, Teck-Peng
, p. 6164 - 6167 (2017)
A visible-light-engaged 2-fold site-selective alkylation of indole derivatives with aliphatic ethers or alcohols has been accomplished for easy access to symmetric 3,3′-bisindolylmethane derivatives. The experimental data suggest a sequential photoredox catalysis induced radical addition and proton-mediated Friedel-Crafts alkylation mechanism.
Nickel-Catalyzed Reductive Cross-Coupling of N-Acyl and N-Sulfonyl Benzotriazoles with Diverse Nitro Compounds: Rapid Access to Amides and Sulfonamides
Qu, Erdong,Li, Shangzhang,Bai, Jin,Zheng, Yan,Li, Wanfang
supporting information, p. 58 - 63 (2021/12/27)
Herein we report a Ni-catalyzed reductive transamidation of conveniently available N-acyl benzotriazoles with alkyl, alkenyl, and aryl nitro compounds, which afforded various amides with good yields and a broad substrate scope. The same catalytic reaction conditions were also applicable for N-sulfonyl benzotriazoles, which could undergo smooth reductive coupling with nitroarenes and nitroalkanes to afford the corresponding sulfonamides.
A facile and versatile electro-reductive system for hydrodefunctionalization under ambient conditions
Huang, Binbin,Guo, Lin,Xia, Wujiong
supporting information, p. 2095 - 2103 (2021/03/26)
A general electrochemical system for reductive hydrodefunctionalization is described, employing the inexpensive and easily available triethylamine (Et3N) as a sacrificial reductant. This protocol is characterized by facile operation, sustainable conditions, and exceptionally wide substrate scope covering the cleavage of C-halogen, N-S, N-C, O-S, O-C, C-C and C-N bonds. Notably, the selectivity and capability of reduction can be conveniently switched by simple incorporation or removal of an alcohol as a co-solvent.
