32183-76-9Relevant academic research and scientific papers
Sustainable Ligand-Free Heterogeneous Palladium-Catalyzed Sonogashira Cross-Coupling Reaction in Deep Eutectic Solvents
Messa, Francesco,Dilauro, Giuseppe,Perna, Filippo M.,Vitale, Paola,Capriati, Vito,Salomone, Antonio
, p. 1979 - 1984 (2020/02/20)
The commercially available and cheap Pd/C was found to promote Sonogashira couplings in the environmentally friendly choline chloride/glycerol eutectic mixture in the absence of external ligands. Under heterogeneous conditions, (hetero)aryl iodides were successfully coupled with both aromatic and aliphatic alkynes in yields ranging from 50 to 99 % within 3 h at 60 °C. The aforementioned catalytic system proved to be effective also towards electron-rich iodides, which are notoriously known to be poorly reactive in Pd-catalyzed Sonogashira coupling reactions. The eutectic mixture and the catalyst could easily and successfully be recycled up to four times with an E-factor as low as 24.4.
Cu2O Nanocrystals-Catalyzed Photoredox Sonogashira Coupling of Terminal Alkynes and Arylhalides Enhanced by CO2
Shanmugam, Munusamy,Sagadevan, Arunachalam,Charpe, Vaibhav Pramod,Pampana, V. Kishore Kumar,Hwang, Kuo Chu
, p. 287 - 292 (2019/11/05)
Herein the first visible-light-activated Sonogashira C?C coupling reaction at room temperature catalyzed by single-metal heterogeneous Cu2O truncated nanocubes (Cu2O TNCs) was developed. A wide variety of aryl halides and terminal alkynes worked well in this recyclable heterogeneous photochemical process to form the corresponding Sonogashira C?C coupling products in good yields. Mechanistic control studies indicated that CO2 enhances the formation of light-absorbing heterogeneous surface-bound CuI-phenylacetylide (λmax=472 nm), which further undergoes single-electron transfer with aryl iodides/bromides to enable Sonogashira Csp2 ?Csp bond formation. In contrast to literature-reported bimetallic TiO2-containing nanoparticles as photocatalyst, this work avoided the need of cocatalysis by TiO2. Single-metal CuI in Cu2O TNCs was solely responsible for the observed Csp2 ?Csp coupling reactions under CO2 atmosphere.
Tertiary amines acting as Alkyl radical equivalents enabled by a P/N heteroleptic Cu(I) photosensitizer
Zheng, Limeng,Jiang, Qinfang,Bao, Hanyang,Zhou, Bingwei,Luo, Shu-Ping,Jin, Hongwei,Wu, Huayue,Liu, Yunkui
supporting information, p. 8888 - 8893 (2020/11/30)
An unprecedented exploration of tertiary amines as alkyl radical equivalents for cross-coupling with aromatic alkynes to access allylarenes has been achieved by a P/N heteroleptic Cu(I)based photosensitizer under photoredox catalysis conditions. Mechanist
3-sulfonylation-indenone compound and preparation method thereof
-
Paragraph 0022; 0023; 0024, (2018/11/03)
The invention discloses a 3-sulfonylation-indenone compound and a preparation method thereof. The preparation method is characterized in that the 3-sulfonylation-indenone compound is synthesized fromortho-aryne benzonitrile and aryl-sulfuryl hydrazine under the actions of copper iodide and tert-butyl hydroperoxide serving as catalysts. The 3-sulfonylation-indenone compound has the advantages of adoption of readily-available raw materials, mild reaction conditions, easiness and convenience in operation, high synthesis yield and contribution to industrial production. The derivative has potential application in the fields of chemical industry and medicine. A method is provided for the synthesis of the 3-sulfonylation-indenone compound for the first time.
Selective synthesis of benzo[4,5]imidazo[2,1-a]isoquinolines via copper-catalyzed tandem annulation of alkynylbenzonitriles with 2-Iodoanilines
Liu, Xiaodong,Deng, Guobo,Liang, Yun
supporting information, p. 2844 - 2847 (2018/06/18)
An efficient copper-catalyzed cascade cyclization reaction for selectively synthesizing a variety of benzo[4,5]imidazo[2,1-a]isoquinoline derivatives has been developed. The reaction features the formation of three different C–N bonds in sequence. In the
A radical cyclization cascade of 2-alkynylbenzonitriles with sodium arylsulfinates
Zhou, Bang,Chen, Wenqi,Yang, Yuzhong,Yang, Yuan,Deng, Guobo,Liang, Yun
supporting information, p. 7959 - 7963 (2018/11/21)
A convenient radical cyclization cascade procedure for the construction of sulfonated indenones from 2-alkynylbenzonitriles and sodium arylsulfinates has been explored under mild reaction conditions. The present methodology offers a low-cost and operationally straightforward approach to synthesizing various sulfonated indenones in moderate to good yields by simple use of cheap sodium persulfate as an oxidant and environmentally benign water as a co-solvent.
Lanthanide-Catalyzed Tandem Insertion of Secondary Amines with 2-Alkynylbenzonitriles: Synthesis of Aminoisoindoles
Ye, Pengqing,Shao, Yinlin,Xie, Leping,Shen, Keting,Cheng, Tianxing,Chen, Jiuxi
, p. 3681 - 3690 (2018/11/23)
A lanthanide-catalyzed intermolecular hydroamination of 2-alkynylbenzonitriles with secondary amines has been disclosed, providing a streamlined access to a range of aminoisoindoles in moderate to excellent yields. The salient features of this reaction in
Silver-mediated radical 5-exo-dig cyclization of 2-alkynylbenzonitriles: Synthesis of phosphinylated 1-indenones
Zhu, Xiao-Tong,Zhao, Qi,Liu, Feng,Wang, Ai-Fang,Cai, Pei-Jun,Hao, Wen-Juan,Tu, Shu-Jiang,Jiang, Bo
supporting information, p. 6828 - 6831 (2017/07/10)
A new silver-mediated 5-exo-dig cyclization of 2-alkynylbenzonitriles with disubstituted phosphine oxide and H2O has been developed. The reaction enables multiple bond-forming events including C-P, C-C and C-O bonds under atmospheric conditions
Copper-catalyzed aerobic oxidative transformation of ketone- Derived N-tosyl hydrazones: An entry to alkynes
Li, Xianwei,Liu, Xiaohang,Chen, Huoji,Wu, Wanqing,Qi, Chaorong,Jiang, Huanfeng
supporting information, p. 14485 - 14489 (2015/02/05)
A novel strategy involving Cu-catalyzed oxidative transformation of ketone-derived hydrazone moiety to various synthetic valuable internal alkynes and diynes has been developed. This method features inexpensive metal catalyst, green oxidant, good functional group tolerance, high regioselectivity and readily available starting materials. Oxidative deprotonation reactions were carried out to form internal alkynes and symmetrical diynes. Cross-coupling reactions of hydrazones with halides and terminal alkynes were performed to afford functionalized alkynes and unsymmetrical conjugated diynes. A mechanism proceeding through a Cu-carbene intermediate is proposed for the CC triple bond formation.
Synthesis of naphthalene amino esters and arylnaphthalene lactone lignans through tandem reactions of 2-alkynylbenzonitriles
He, Yan,Zhang, Xinying,Fan, Xuesen
supporting information, p. 5641 - 5643 (2014/05/20)
Tandem reaction of 2-alkynylbenzonitriles with a Reformatsky reagent turned out to be a novel and efficient approach toward 1-aminonaphthalene-2- carboxylates. Interestingly, with 2-(3-hydroxyprop-1-ynyl)benzonitriles as the substrates, a more sophisticat
