2040-37-1Relevant academic research and scientific papers
Organocatalysis Linked to Charge-Enhanced Acidity with Superelectrophilic Traits
Smajlagic, Ivor,White, Brandon,Azeez, Oyindamola,Pilkington, Melanie,Dudding, Travis
, p. 1128 - 1138 (2022/01/19)
Hydrogen bonding is ubiquitous throughout nature and serves as a versatile platform for accessing chemical reactivity. In leveraging this force, chemists have utilized organocatalysts to expand the spectrum of chemical reactivity enabled by hydrogen bondi
Iodine catalysed synthesis of unsymmetrical benzylic ethers by direct cross-coupling of alcohols
Kharrngi, Balamphrang,Basumatary, Grace,Bez, Ghanashyam
supporting information, (2021/09/13)
Although symmetrical ethers can be synthesized easily from alcohols, synthesis of unsymmetrical ethers by dehydrative cross-coupling of alcohols is still a challenge. While dehydrative cross-coupling is environmentally appealing due to formation of water as the only byproduct, the chances for formation of symmetrical ethers always exist. The existing transition metal based methods give good selectivity, but the catalyst are costly and not readily available. Here, we present a simple, readily available, and cost-effective catalyst in the form of molecular iodine which catalyzes a highly selective cross-coupling of benzylic alcohols with benzyl, alkyl, and aryl alcohols to give their corresponding unsymmetrical ethers in good to excellent yield.
Intramolecular activation of imidate with cationic gold(I) catalyst: A new benzylation reaction of alcohols
Ban, Shintaro,Endo, Tomotake,Matsui, Rikako,Morita, Nobuyoshi,Hashimoto, Yoshimitsu,Tanaka, Kosaku,Tamura, Osamu
, (2020/08/28)
Benzylation of alcohols with benzyl (Z)-2,2,2-trifluoro-N-(2-alkynylphenyl)acetimidates 5a-f in the presence of a cationic gold(I) catalyst was investigated. Reagent 5f was the most effective, affording benzyl ethers in good yields. Our results indicate that these gold(I)-activated imidates are effective leaving groups.
Development of triazine-based benzylating reagents possessing T-butyl group on the triazine core: Thermally controllable reagents for the initiation of reaction
Karuo, Yukiko,Yamada, Kohei,Kunishima, Munetaka
, p. 303 - 308 (2018/03/09)
Benzylating reagents, 4-(4,6-di-t-butyl-1,3,5-triazin-2-yl)-4-benzylmorpholinium triflate, and related derivatives have been developed. The reagents release benzyl triflate as a benzyl cation equivalent upon heating the solution to 40°C under neutral conditions. The O-benzylation of alcohols using a stoichiometric amount of these reagents afforded corresponding benzyl ethers in good to high yields. This was due to the presence of a bulky t-butyl group on the triazine ring of these reagents that prevents the consumption of benzyl triflate via a side reaction with a morpholinotriazine derivative.
B(C6F5)3 catalyzed direct nucleophilic substitution of benzylic alcohols: an effective method of constructing C-O, C-S and C-C bonds from benzylic alcohols
Meng, Shan-Shui,Wang, Qian,Huang, Gong-Bin,Lin, Li-Rong,Zhao, Jun-Ling,Chan, Albert S. C.
, p. 30946 - 30949 (2018/09/13)
An efficient and general method of nucleophilic substitution of benzylic alcohols catalyzed by non-metallic Lewis acid B(C6F5)3 was developed. The reaction could be carried out under mild conditions and more than 35 exampl
Cp*CoIII-Catalyzed Efficient Dehydrogenation of Secondary Alcohols
Gangwar, Manoj Kumar,Dahiya, Pardeep,Emayavaramban, Balakumar,Sundararaju, Basker
supporting information, p. 2445 - 2448 (2018/09/10)
A novel, well-defined molecular Cp*CoIII complex was isolated and structurally characterized for the first time. The efficiency of this cobalt catalyst was demonstrated in the alcohol dehydrogenation and dehydrative coupling of secondary alcohols under mild conditions into ketones and ethers, respectively.
Method for catalyzing etherification of benzyl alcohol compounds
-
Paragraph 0032; 0033; 0034, (2018/11/22)
The invention belongs to the field of organic synthesis and discloses a method for catalyzing the etherification of benzyl alcohol compounds. The benzyl alcohol compounds are mixed with an alcohol compound A, and a solvent and tripentafluorophenylborane s
W-Ti-O mixed metal oxide catalyzed dehydrative cross-etherification of alcohols
Yada, Akira,Murayama, Toru,Hirata, Jun,Nakashima, Takuya,Tamura, Masanori,Kon, Yoshihiro,Ueda, Wataru
supporting information, p. 447 - 449 (2018/03/27)
A dehydrative cross-etherification reaction of two different alcohols is achieved in the presence of hydrothermally synthesized tungsten-titanium mixed metal oxide (W-Ti-O) catalyst. The reaction is environmentally benign: organic solvent is not necessary and the catalyst is readily recovered and reusable.
Nickel-Catalyzed Reductive Etherification of Aldehydes at Room Temperature: C-O vs C-C Bond Formation
Rahimi, Sajjad,Panahi, Farhad,Bahmani, Marzieh,Iranpoor, Nasser
, p. 973 - 979 (2018/01/27)
The reaction of secondary and tertiary benzyl alcohols activated by 2,4,6-trichloro-1,3,5-triazine (TCT) with aldehydes in the presence of NiCl2·dmg as a precatalyst in ethylene glycol afforded ethers at room temperature. A selective C-O vs C-C bond formation was observed for the secondary and tertiary benzyl alcohols in comparison with primary ones.
N,N′-Dimethylated Benzyloxytriazinedione: A Stable Solid Reagent for Acid-Catalyzed O-Benzylation
Fujita, Hikaru,Kakuyama, Satoshi,Kunishima, Munetaka
supporting information, p. 833 - 839 (2017/02/15)
N,N′-Dimethylated 6-(benzyloxy)-1,3,5-triazine-2,4(1H,3H)-dione (DMBOT) has been developed as a triazinedione-based, stable solid reagent for acid-catalyzed O-benzylation. The conceptual basis of the design was to fix the core triazinedione skeleton, and
