53924-28-0Relevant academic research and scientific papers
Halogen bonding organocatalysis enhanced through intramolecular hydrogen bonds
Berryman, Orion B.,Decato, Daniel A.,Riel, Asia Marie S.,Sun, Jiyu
supporting information, p. 1378 - 1381 (2022/02/09)
Recent results indicate a halogen bond donor is strengthened through direct interaction with a hydrogen bond to the electron-rich belt of the halogen. Here, this Hydrogen Bond enhanced Halogen Bond (HBeXB) plays a clear role in a catalyst. Our HBeXB catalyst improves product conversion in a halide abstraction reaction over a traditional halogen bonding derivative. This journal is
Zirconium-catalysed direct substitution of alcohols: enhancing the selectivity by kinetic analysis
Camaj, David,Carlsson, Robin,Dalla-Santa, Oscar,Lill, Malin,Lundberg, Helena,Margarita, Cristiana,Ramstr?m, Anja,Tu?on, Hernando,Villo, Piret
, p. 7420 - 7430 (2021/11/23)
Kinetic analysis was used as a tool for rational optimization of a catalytic, direct substitution of alcohols to enable the selective formation of unsymmetrical ethers, thioethers, and Friedel-Crafts alkylation products using a moisture-tolerant and commercially available zirconium complex (2 to 8 mol%). Operating in air and in the absence of dehydration techniques, the protocol furnished a variety of products in high yields, including glycosylated alcohols and sterically hindered ethers. In addition, the kinetic studies provided mechanistic insight into the network of parallel transformations that take place in the reaction, and helped to elucidate the nature of the operating catalyst.
An efficient synthesis of medicinally important indole based triarylmethanes by using propylphosphonic anhydride (T3P)
Cheruku, Srinivas,Nagaraju, Chaithra,Shetty, Poornima,Hassan A, Swarup,Nagarakere C, Sandhya,Manikyanally N, Kumara,Kempegowda, Mantelingu
supporting information, p. 1486 - 1494 (2020/04/08)
We have developed an economical and efficient method for the synthesis of medicinally and synthetically important indole-based triarylmethanes by using indoles and benzhydrols in the presence of propylphosphonic anhydride (T3P). This methodolog
Gold(III)-Catalyzed Decarboxylative C3-Benzylation of Indole-3-carboxylic Acids with Benzylic Alcohols in Water
Hikawa, Hidemasa,Kotaki, Fumiya,Kikkawa, Shoko,Azumaya, Isao
supporting information, p. 1972 - 1979 (2019/05/16)
A strategy for the gold(III)-catalyzed decarboxylative coupling reaction of indole-3-carboxylic acids with benzylic alcohols has been developed. This cascade reaction is devised as a straightforward and efficient synthetic route for 3-benzylindoles in moderate to excellent yields (50-93%). A Hammett study of the protodecarboxylation gives a negative ρ value, suggesting that there is a buildup of positive charge on the indole ring in the transition state. Furthermore, comparison of initial rates in H2O and in D2O reveals an observed kinetic solvent isotope effect (KSIE = 2.7). This simple protocol, which affords the desired products with CO2 and water as the coproducts, can be achieved under mild conditions without the need for base or other additives in water.
Fluorinated Alcohol-Promoted Reaction of Chlorohydrocarbons with Diverse Nucleophiles for the Synthesis of Triarylmethanes and Tetraarylmethanes
Yu, Liping,Li, Shuai-Shuai,Li, Weina,Yu, Shitao,Liu, Qing,Xiao, Jian
, p. 15277 - 15283 (2019/01/04)
This article reports an efficient synthesis of triarylmethanes and tetraarylmethanes from chlorohydrocarbons with miscellaneous nucleophiles in fluorinated alcohols, featuring metal-free, wide substrate scope, excellent functional group tolerance, and mild reaction conditions.
Easy access to a library of alkylindoles: Reductive alkylation of indoles with carbonyl compounds and hydrosilanes under indium catalysis
Nomiyama, Shota,Hondo, Takehiro,Tsuchimoto, Teruhisa
, p. 1136 - 1149 (2016/04/19)
By applying carbonyl compounds as sources of alkyl groups to the indium-catalyzed reductive alkylation of indoles, a reliable and practical method capable of offering a wide range of alkylindoles with structural diversity has been developed. An important
An efficient iron-promoted synthesis of 6H-indolo[2,3- b] quinolines and neocryptolepine derivatives
Yan, Zicong,Wan, Changfeng,Wan, Jianyong,Wang, Zhiyong
supporting information, p. 4405 - 4408 (2016/06/06)
A facile and practical method for the preparation of 6H-indolo[2,3-b]quinolines and neocryptolepines was developed under the promotion of the easily available ferric trichloride, affording the desired products with moderate to good yields.
Br2-Catalyzed regioselective dehydrative coupling of indoles with acyloins: Direct synthesis of α-(3-indolyl) ketones
Liang, Deqiang,Li, Xiangguang,Li, Yanni,Yang, Yungang,Gao, Shulin,Cheng, Ping
, p. 29020 - 29025 (2017/07/03)
An efficient Br2-catalyzed synthesis of α-(3-indolyl) ketones via dehydrative coupling of simple indoles with acyloins is presented. This reaction proceeded with high C-3 selectivity and a wide substrate scope, and without any metal catalyst. B
Organocatalytic friedel-crafts benzylation of heteroaromatic and aromatic compounds via an SN1 pathway
Watanabe, Naruhisa,Matsugi, Aoi,Nakano, Keiji,Ichikawa, Yoshiyasu,Kotsuki, Hiyoshizo
supporting information, p. 438 - 442 (2014/03/21)
The Friedel-Crafts-type benzylation of various π-excessive heteroaromatic and aromatic compounds with trityl or benzhydryl halides was efficiently promoted by a thiourea catalyst. This is a novel example of thiourea catalysis of aromatic alkylation by way
Solvent-free Br?nsted acid catalysed alkylation of arenes and heteroarenes with benzylic alcohols
Barbero, Margherita,Cadamuro, Silvano,Dughera, Stefano,Rucci, Marta,Spano, Giulia,Venturello, Paolo
, p. 1818 - 1826 (2014/03/21)
A simple and efficient alkylation of aromatic and heteroaromatic compounds via the direct SN1-type nucleophilic substitution of benzylic alcohols in the presence of catalytic amounts of the strong Br?nsted acid o-benzenedisulfonimide under neat conditions is herein reported. A library of di- and triaryl (and heteroaryl) methanes was prepared in good yields and high regioselectivity. The observed reactivity was shown to be in agreement with Mayr's nucleophilicity and electrophilicity scales.
