59647-77-7Relevant articles and documents
Palladium-Catalyzed Cascade Dearomative Spirocyclization and C?H Annulation of Aromatic Halides with Alkynes
Liao, Xingrong,Zhou, Fulin,Bin, Zhengyang,Yang, Yudong,You, Jingsong
supporting information, p. 5203 - 5207 (2021/07/19)
Described herein is a palladium-catalyzed intermolecular dearomative annulation of aryl halides with alkynes, which provides a rapid approach to a class of structurally unique spiroembedded polycyclic aromatic compounds. The cascade process is accomplished by a sequential alkyne migratory insertion, Heck-type dearomatization, and C-H bond annulation. Further optoelectronic study indicated this fused spirocyclic scaffold could be a potential host material for OLEDs, as exemplified by a fabricated red PhOLED device with a maximum external quantum efficiency of 23.0%.
Synthesis of Diarylethynes from Aryldiazonium Salts by Using Calcium Carbide as an Alkyne Source in a Deep Eutectic Solvent
Ma, Xiaolong,Li, Zheng
supporting information, p. 631 - 635 (2020/12/28)
An efficient method for the synthesis of diarylethynes from aryldiazonium salts by using calcium carbide as an alkyne source at room temperature in a deep eutectic solvent is described. The salient features of this protocol are an inexpensive and easy-to-handle alkyne source, a nonvolatile and recyclable solvent, mild conditions, and a simple workup procedure.
Rhodium-Catalyzed Regioselective Hydroformylation of Alkynes to α,β-Unsaturated Aldehydes Using Formic Acid
Fan, Chao,Hou, Jing,Chen, Yu-Jia,Ding, Kui-Ling,Zhou, Qi-Lin
supporting information, p. 2074 - 2077 (2021/04/05)
A rhodium-catalyzed hydroformylation of alkynes with formic acid was developed. The method provides α,β-unsaturated aldehydes in high yield and E-selectivity without the need to handle toxic CO gas.
Synthesis of Bidentate Nitrogen Ligands by Rh-Catalyzed C-H Annulation and Their Application to Pd-Catalyzed Aerobic C-H Alkenylation
Kim, Hyun Tae,Kang, Eunsu,Kim, Minkyu,Joo, Jung Min
supporting information, p. 3657 - 3662 (2021/05/10)
A new class of bidentate ligands was prepared by a modular approach involving Rh-catalyzed C-H annulation reactions. The resulting conformationally constrained ligands enabled the Pd-catalyzed C-H alkenylation at electron-rich and sterically less hindered positions of electron-rich arenes while promoting the facile oxidation of Pd(0) intermediates by oxygen. This newly introduced ligand class is complementary to the ligands developed for Pd-catalyzed oxidative reactions and may find broad application in transition-metal-catalyzed reactions.
Rh(iii)-Catalyzed three-component cascade annulation to produce theN-oxopropyl chain of isoquinolone derivatives
He, Yuan,Liao, Xian-Zhang,Dong, Lin,Chen, Fen-Er
supporting information, p. 561 - 567 (2021/02/06)
Developing powerful methods to introduce versatile functional groups at theN-substituents of isoquinolone scaffolds is still a great challenge. Herein, we report a novel three-component cascade annulation reaction to efficiently construct theN-oxopropyl chain of isoquinolone derivativesviarhodium(iii)-catalyzed C-H activation/cyclization/nucleophilic attack, with oxazoles used both as the directing group and potential functionalized reagents.
Rhodium-Catalyzed Spiro Indenyl Benzoxazine Synthesis via C-H Activation/Annulation of 3-Aryl-2H-Benzo[b][1,4]oxazines and Alkynes
Tan, Heng,Laishram, Ronibala Devi,Zhang, Xuexin,Shi, Guangrui,Li, Kangkui,Chen, Jingchao
supporting information, p. 4542 - 4546 (2020/07/04)
The rhodium (III)-catalyzed annulation of 3-Aryl-2H-Benzo[b][1,4]oxazines with alkynes via C–H activation has been developed. This reaction afforded a series of spiro indenyl benzoxazine in high yields under mild reaction condition with good functional group tolerance.
The ruthenium(ii)-catalyzed C-H olefination of indoles with alkynes: The facile construction of tetrasubstituted alkenes under aqueous conditions
Li, Ming,Yao, Tian-Yu,Sun, Sheng-Zheng,Yan, Ting-Xun,Wen, Li-Rong,Zhang, Lin-Bao
supporting information, p. 3158 - 3163 (2020/05/08)
An environmentally-friendly and facile protocol for the construction of tetrasubstituted alkenes has been established with Ru(ii)-catalyzed C-H bond functionalizations under mild conditions. The method features the usage of readily available substrates, without external oxidants and additives, 100% atom economy, and excellent regioselectivity, thus enhancing the practicability of this protocol. Moreover, this transformation proceeded smoothly under aqueous conditions and could be extended to the gram scale. N-Methoxyamide, as a directing group (DG), played a vital role in the transformation.
Photo-induced and Rapid Labeling of Tetrazine-Bearing Proteins via Cyclopropenone-Caged Bicyclononynes
Mayer, Susanne V.,Murnauer, Anton,von Wrisberg, Marie-Kristin,Jokisch, Marie-Lena,Lang, Kathrin
supporting information, p. 15876 - 15882 (2019/10/28)
Inverse electron-demand Diels–Alder cycloadditions (iEDDAC) between tetrazines and strained alkenes/alkynes have emerged as essential tools for studying and manipulating biomolecules. A light-triggered version of iEDDAC (photo-iEDDAC) is presented that confers spatio-temporal control to bioorthogonal labeling in vitro and in cellulo. A cyclopropenone-caged dibenzoannulated bicyclo[6.1.0]nonyne probe (photo-DMBO) was designed that is unreactive towards tetrazines before light-activation, but engages in iEDDAC after irradiation at 365 nm. Aminoacyl tRNA synthetase/tRNA pairs were discovered for efficient site-specific incorporation of tetrazine-containing amino acids into proteins in living cells. In situ light activation of photo-DMBO conjugates allows labeling of tetrazine-modified proteins in living E. coli. This allows proteins in living cells to be modified in a spatio-temporally controlled manner and may be extended to photo-induced and site-specific protein labeling in animals.
Production method of diaryl alkyne compound
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Paragraph 0074-0075; 0081, (2019/10/01)
The invention discloses a production method of a diaryl alkyne compound. The production method of the diaryl alkyne compound comprises the steps of under protection of nitrogen, placing a bromobenzenesubstrate, alkynol, a palladium catalyst, an organic phosphine ligand and inorganic alkali into a reaction container, then adding a solvent, heating the reaction container for reaction, after the reaction container is cooled to room temperature, adding a saturated ammonium chloride solution for quenching, and then conducting extraction and column chromatography isolation and purification to obtain the diaryl alkyne compound. According to the production method of the diaryl alkyne compound, the aryl bromide and the alkynol which are simple and easy to obtain are used as raw materials, and through the palladium-catalyzed coupling reaction, the diaryl alkyne compound is obtained. The reaction raw materials are simple and easy to obtain, reaction conditions are mild, several defects in a traditional synthesis method are overcome, for example, the defect that when calcium carbide is used as a raw material, the release speed of acetylene cannot be controlled is overcome, the defect that when terminal alkyne is used as a raw material, a product and the raw material are hard to separate due to similar polarity is overcome, and the like. The method also has good performance in amplification reaction, so that the method has great application prospects.
Palladium-catalyzed sequential three-component reactions to access vinylsilanes
Zhou, Bo,Lu, Ailan,Shao, Changdong,Liang, Xinda,Zhang, Yanghui
, p. 10598 - 10601 (2018/09/25)
A palladium-catalyzed sequential three-component reaction has been developed. The palladacycles, generated through cascade reactions of aryl halides and alkynes, are the key intermediates and react with hexamethyldisilane to form disilylated products. The reaction represents a useful preparative method for vinylsilanes, and the vinylsilanes can be transformed into tetrasubstituted alkenes.
