127229-97-4Relevant academic research and scientific papers
Palladium-Catalyzed Synthesis of 6H-Dibenzo[c,h]chromenes and 5,6-Dihydrobenzo[c]phenanthridines: Application to the Synthesis of Dibenzo[c,h]chromene-6-ones, Benzo[c]phenanthridines, and Arnottin I
Pramanik, Subhendu,Jash, Moumita,Mondal, Debasmita,Chowdhury, Chinmay
, p. 5223 - 5238 (2019)
6H-Dibenzo[c,h]chromenes and 5,6-dihydrobenzo[c]phenanthridines have been synthesized via Palladium (II)-catalyzed domino reactions of acetylenic substrates involving intramolecular trans-oxo/amino palladation onto the triple bond followed by nucleophilic
Structure and Reactivity of N-Heterocyclic Alkynyl Hypervalent Iodine Reagents
Le Du, Eliott,Duhail, Thibaut,Wodrich, Matthew D.,Scopelliti, Rosario,Fadaei-Tirani, Farzaneh,Anselmi, Elsa,Magnier, Emmanuel,Waser, Jerome
supporting information, p. 10979 - 10986 (2021/06/08)
Ethynylbenziodoxol(on)e (EBX) cyclic hypervalent iodine reagents have become popular reagents for the alkynylation of radicals and nucleophiles, but only offer limited possibilities for further structure and reactivity fine-tuning. Herein, the synthesis o
Synthesis of N-Heteroaromatic Compounds through Cyclocarbonylative Sonogashira Reactions
Aronica, Laura Antonella,Albano, Gianluigi,Giannotti, Luca,Meucci, Elisa
supporting information, p. 955 - 963 (2017/02/15)
A protocol based on cyclocarbonylative Sonogashira reactions has been developed for the synthesis of nitrogen-containing heterocycles. The process is carried out under CO pressure, in the presence of a small amount of PdCl2(PPh3)sub
Metal-free direct N-benzylation of sulfonamides with benzyl alcohols by employing boron trifluoride-diethyl ether complex
Pan, Jing,Li, Jia-Qiang,Huang, Ruo-Feng,Zhang, Xiao-Hui,Shen, Hang,Xiong, Yan,Zhu, Xiang-Ming
supporting information, p. 1101 - 1108 (2015/04/14)
N-Benzylation of sulfonamides with both primary and secondary benzyl alcohols by employing boron trifluoride-diethyl ether complex under mild reaction conditions has been developed, which is an environmentally benign and facile protocol for assembling a series of primary and secondary benzyl sulfonamides in yields up to 83%. In this coupling reaction, the beneficial role of water has been clarified in detail through control experiments.
Palladium-catalyzed cyclization of vinyl iodide-tethered allensulfonamide
Xie, Zheng,Wu, Pan,Cai, Liangzhen,Tong, Xiaofeng
supporting information, p. 2160 - 2162 (2014/04/03)
This Letter describes a palladium-catalyzed cyclization of vinyl iodide-tethered allensulfonamide in the presence of alkylol, which provides a facile access to 2-alkoxy-3-methylene-tetrahydropyridine. The asymmetric version of this reaction has also been preliminarily realized with up to 81% enantioselectivity when chiral bisphosphine ligands were used.
Ti/Ni-mediated inter- and intramolecular conjugate addition of aryl and alkenyl halides and triflates
Marquez, Irene R.,Miguel, Delia,Millan, Alba,Marcos, M. Luisa,De Cienfuegos, Luis Alvarez,Campana, Araceli G.,Cuerva, Juan M.
, p. 1529 - 1541 (2014/03/21)
In this work, we show that the unique combination of a nickel catalyst and Cp2TiCl allows the direct conjugate addition of aryl and alkenyl iodides, bromides, and to a lesser extent, chlorides and triflates to α,β-unsaturated carbonyls at room temperature, without requiring the previous formation of an organometallic nucleophile. The reaction proceeds inter- and intramolecularly with good functional group compatibility, which is key for the development of free protecting group methodologies. Carbo- and heterocycles of five- and six-membered rings are obtained in good yields. Moreover, some insights about the mechanism involved have been obtained from cyclic voltammetry, UV-vis, and HRTEM measurements.
Efficient access to 1,4-benzothiazine: Palladium-catalyzed double C-S bond formation using Na2S2O3 as sulfurating reagent
Qiao, Zongjun,Liu, Hui,Xiao, Xiao,Fu, Yana,Wei, Jianpeng,Li, Yuxue,Jiang, Xuefeng
supporting information, p. 2594 - 2597 (2013/07/19)
A novel Pd-catalyzed double C-S bond formation coupling reaction has been developed. This protocol, in which Na2S2O3 was used as sulfurating reagent in metal-catalyzed reactions, provides an efficient method for the synthe
Diphosphine-catalyzed mixed double-michael reaction: A unified synthesis of lndolines, Dihydropyrrolopyridines, Benzimidazolines, Tetrahydroquinolines, Tetrahydroisoquinolines, Dihydrobenzo-1,4-oxazines, and Dihydrobenzo-3,1- oxazines
Sriramurthy, Vardhineedi,Kwon, Ohyun
supporting information; experimental part, p. 1084 - 1087 (2010/06/15)
(Figure Presented) Seven different types of benzannulated N-heterocycles-indolines, dihydropyrrolopyridlnes, benzimidazolines, dihydrobenzo-3,1-oxazines, benzomorpholines, tetrahydroquinolines, and tetrahydroisoquinolines-can be obtained from simple dinuc
Synthesis of polycyclic sultams by palladium-catalyzed intramolecular cyclization
Majumdar,Mondal, Shovan,De, Nirupam
experimental part, p. 3127 - 3135 (2009/12/27)
A practical and high-yielding method for the synthesis of new sultams from readily available sulfonamides, 1-naphthylamine, and 2-halobenzyl bromides is reported. A variety of tricyclic, tetracyclic, and pentacyclic sultams have been prepared via palladiumcatalyzed, ligand-free intramolecular cyclization. Detailed mechanistic studies of the reaction pathway are also described.
Cyclization reactions of 2-alkynylbenzyl alcohol and 2-alkynylbenzylamine derivatives promoted by tetrabutylammonium fluoride
Hiroya, Kou,Jouka, Rumi,Kameda, Mitsuyoshi,Yasuhara, Akito,Sakamoto, Takao
, p. 9697 - 9710 (2007/10/03)
The regioselectivity of the cyclization reaction of 2-ethynylbenzyl alcohol and 2-ethynylbenzylamine derivatives promoted by TBAF was investigated. Six-membered ring derivatives were obtained from the compounds, which have a butyl group on the triple bond. Whereas five-membered ring products were afforded from the substrates having hydrogen or aromatic substituents on the acetylene moiety. It was also concluded that both the tetrabutylammonium cation and fluoride anion were essential for the cyclization. Thus, the actual mechanism and catalytic cycle were also suggested.
