89691-67-8Relevant academic research and scientific papers
Derivatizing Tribenzothiophene-Fused Hexa-peri-hexabenzocoronenes with Tunable Optoelectronic Properties
Liu, Yi,Marszalek, Tomasz,Müllen, Klaus,Pisula, Wojciech,Feng, Xinliang
, p. 2107 - 2112 (2016)
A series of trisbenzothieno[1,2:7,8:13,14]hexa-peri-hexabenzocoronenes were synthesized and characterized by a combination of NMR, 2D NMR, MALDI-TOF MS, UV/Vis absorption spectroscopy, and 2D-WAXS measurement. By structural modulation like decoration of e
Catalyst- and acid-free Markovnikov hydration of alkynes in a sustainable H2O/ethyl lactate system
Dandia, Anshu,Saini, Pratibha,Chithra,Vennapusa, Sivaranjana Reddy,Parewa, Vijay
, (2021/03/15)
An efficient and sustainable protocol for the hydration of alkynes has been developed under metal/acid/catalyst/ligand-free conditions in a water/ethyl lactate mixture. The hydrogen-bond network in the ethyl lactate and water mixture plays a crucial and decisive role in activating the alkynes for hydration to afford the corresponding methyl ketones. This strategy gives the Markovnikov (ketone) addition product selectively over other possible products. The essential role of hydrogen bonding has been confirmed by experimental and theoretical techniques. A probable mechanism has been suggested by various control tests. The efficacy of the method has been further explored for the competent production of value-added α,β-unsaturated carbonyl compounds through the reaction of aldehydes with alkynes as ketonic surrogates. The environmentally benign hydration method takes place under mild conditions, has broad functional-group compatibility, and uses the ethyl lactate/water (1:3) medium as a “green alternative” in the absence of any hazardous, harmful, or expensive substances.
The intramolecular reaction of acetophenoneN-tosylhydrazone and vinyl: Br?nsted acid-promoted cationic cyclization toward polysubstituted indenes
Wang, Zhixin,Li, Yang,Chen, Fan,Qian, Peng-Cheng,Cheng, Jiang
, p. 1810 - 1813 (2021/02/27)
In the presence of TsNHNH2, a Br?nsted acid-promoted intramolecular cyclization ofo-(1-arylvinyl) acetophenone derivatives was developed, leading to polysubstituted indenes with complexity and diversity in moderate to excellent yields. In sharp contrast with either the radical or carbene involved cyclization of aldehydicN-tosylhydrazone with vinyl, a cationic cyclization pathway was involved, whereN-tosylhydrazone served as an electrophile and alkylation reagent during this transformation.
α-Oxocarboxylic Acids as Three-Carbon Insertion Units for Palladium-Catalyzed Decarboxylative Cascade Synthesis of Diverse Fused Heteropolycycles
Zhou, Liwei,Qiao, Shujia,Zhou, Fengru,Xuchen, Xinyu,Deng, Guobo,Yang, Yuan,Liang, Yun
, p. 2878 - 2883 (2021/05/05)
A novel palladium-catalyzed decarboxylative cascade cyclization for the assembly of diverse fused heteropolycycles by employing α-oxocarboxylic acids as three-carbon insertion units is reported. This protocol enables the synthesis of isoquinolinedione- and indolo[2,1-a]isoquinolinone-fused benzocycloheptanones in moderate to good yields by the use of different aryl iodides, including alkene-tethered 2-iodobenzamides and 2-(2-iodophenyl)-1H-indoles. Notably, the approach achieves simultaneous construction of both six- and seven-membered rings via sequential intramolecular carbopalladation, C-H activation, and decarboxylation.
Divergent Access to Benzocycles through Copper-Catalyzed Borylative Cyclizations
Yoon, Wan Seok,Han, Jung Tae,Yun, Jaesook
, p. 4953 - 4959 (2021/09/14)
A copper-catalyzed chemodivergent approach to five- and six-membered benzocycles from dienyl arenes tethered with a ketone has been developed. Through proper choice of coordinating ligands and catalytic conditions, copper-catalyzed borylative cyclization of a single dienyl arene can be diverted to two different pathways, leading to indanols and dihydronaphthalenols with high stereoselectivity. The chiral bidentate bisphosphine ligand (S,S)-Ph-BPE was optimal for asymmetric copper-allyl addition to a tethered ketone via a boat-like transition state, whereas NHC ligands led to boro-allyl addition producing indanols with high diastereoselectivity. (Figure presented.).
Atmosphere-Controlled Palladium-Catalyzed Divergent Decarboxylative Cyclization of 2-Iodobiphenyls and α-Oxocarboxylic Acids
Zhou, Liwei,Sun, Mingjie,Zhou, Fengru,Deng, Guobo,Yang, Yuan,Liang, Yun
, p. 7150 - 7155 (2021/09/18)
A novel palladium-catalyzed divergent decarboxylative cyclization of 2-iodobiphenyls and α-oxocarboxylic acids utilizing the atmosphere as a controlled switch is reported. Under the protection of a nitrogen atmosphere, tribenzotropones are synthesized by a [4 + 3] decarboxylative cyclization. Employing a palladium/O2 system enables a [4 + 2] decarboxylative cyclization to assemble triphenylenes. Notably, preliminary mechanistic studies indicate that the formation of triphenylenes involves a double decarboxylation.
Asymmetric Synthesis and Application of Chiral Spirosilabiindanes
Chang, Xin,Chen, Hong-Chao,Li, Chuan-Ying,Ma, Pei-Long,Wang, Peng
, p. 8937 - 8940 (2020/04/30)
Reported here is the development of a class of chiral spirosilabiindane scaffolds by Rh-catalyzed asymmetric double hydrosilation, for the first time. Enantiopure SPSiOL (spirosilabiindane diol), a new type of chiral building block for the preparation of various chiral ligands and catalysts, was readily prepared on greater than 10 gram scale using this protocol. The potential of this new spirosilabiindane scaffold in asymmetric catalysis was preliminarily demonstrated by development of the corresponding monodentate phosphoramidite ligands (SPSiPhos), which were used in both a Rh-catalyzed hydrogenation and a Pd-catalyzed intramolecular carboamination.
Synthesis of fluorenyl alcohols: Via cooperative palladium/norbornene catalysis
Casnati, Alessandra,Fontana, Marco,Motti, Elena,Della Ca, Nicola
, p. 6165 - 6173 (2019/07/04)
Herein, we report a novel catalytic synthesis of substituted 9H-fluoren-9-ols starting from aryl iodides and secondary ortho-bromobenzyl alcohols in the presence of palladium/norbornene as a catalytic system. The present protocol exhibits high functional
Air-stable μ2-hydroxyl bridged cationic binuclear complexes of zirconocene perfluorooctanesulfonates: their structures, characterization and application
Zhang, Xiaohong,Xu, Xinhua,Li, Ningbo,Liang, Zhiwu,Tang, Zilong
supporting information, p. 1926 - 1932 (2018/03/21)
Three air-stable zirconocene perfluoro-octanesulfonates were successfully synthesized by treatment of C8F17SO3Ag with (RCp)2ZrCl2 [R = H, n-Bu, t-Bu]. According to X-ray analysis, they have μ2-hydroxyl bridged cationic binuclear structures: (i) [CpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·2THF·4H2O (1a·2THF·4H2O), (ii) [n-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·6H2O (2a·6H2O), and (iii) [t-BuCpZr(OH2)3]2(μ2-OH)2(OSO2C8F17)4·2C3H6O·8H2O (3a·2C3H6O·8H2O). The ligands of water and organic molecules in the complexes originated from the moist air and solvent during their recrystallization. These complexes were characterized with different techniques, and found to show water tolerance, air/thermal stability as well as strong Lewis acidity. Moreover, the complexes showed highly catalytic activity in various reactions of C–C bond formation. With good recyclability, they should find wide applications in organic chemistry.
PdII-Catalyzed Oxidative Tandem aza-Wacker/Heck Cyclization for the Construction of Fused 5,6-Bicyclic N,O-Heterocycles
Ye, Chenghao,Kou, Xuezhen,Xia, Jingzhao,Yang, Guoqiang,Kong, Li,Wei, Quhao,Zhang, Wanbin
, p. 1897 - 1901 (2018/07/31)
A PdII-catalyzed oxidative tandem cyclization was developed for the construction of fused 5,6-bicyclic N, O-heterocycles. This reaction was enabled by the combined use of a 3-methylpyridine ligand and pentafluorobenzoic acid additive. A range of heterocyclic products with different substituents could be prepared in moderate to good yields via this methodology. Several transformations, including a scaled-up preparation of product 2 a, were also carried out showing the good applicability of our methodology.
