Organic & Biomolecular Chemistry, Год журнала: 2024, Номер unknown
Опубликована: Янв. 1, 2024
An efficient route to the metal-free hydroboration and cyanosilylation of a wide range alkynyl trifluoromethyl ketones using HBpin trimethylsilyl cyanide under mild reaction conditions at ambient temperature with higher yields is reported.
Язык: Английский
Chemical Society Reviews, Год журнала: 2022, Номер 51(21), С. 8877 - 8922
Опубликована: Янв. 1, 2022
This review covers the development of transition metal-catalysed hydroboration reaction, from its beginnings in 1980s to more recent developments including earth-abundant catalysts and an ever-expanding array substrates.
Язык: Английский
Процитировано
150
Green Chemistry, Год журнала: 2020, Номер 22(16), С. 5210 - 5224
Опубликована: Янв. 1, 2020
Hydroelementation enables a facile reduction or functionalization of several unsaturated systems, and thus activation such bonds like B–H Si–H is powerful synthetic tool.
Язык: Английский
Процитировано
98
Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(18), С. 3675 - 3702
Опубликована: Янв. 1, 2022
Catalytic hydroboration of imines, nitriles, and carbodiimides are reviewed as powerful tools for preparation amines.
Язык: Английский
Процитировано
33
The Journal of Organic Chemistry, Год журнала: 2020, Номер 85(17), С. 11200 - 11210
Опубликована: Авг. 6, 2020
Three new dimeric bis-guanidinate zinc(II) alkyl, halide, and hydride complexes [LZnEt]2 (1), [LZnI]2 (2) [LZnH]2 (3) were prepared. Compound 3 was successfully employed for the hydrosilylation hydroboration of a vast number ketones. The catalytic performance in acetophenone exhibits turnover frequency, reaching up to 5800 h–1, outperforming that reported zinc catalysts. Notably, both intra- intermolecular chemoselective reactions have been investigated.
Язык: Английский
Процитировано
46
The Journal of Organic Chemistry, Год журнала: 2022, Номер 87(19), С. 13259 - 13269
Опубликована: Сен. 12, 2022
Investigation of a variety Lewis acids for the hydroboration-hydrolysis (reduction) ketones with amine-boranes has revealed that catalytic (10 mol %) titanium tetrachloride (TiCl4) in diethyl ether at room temperature immensely accelerates reaction ammonia borane. The product alcohols are produced good to excellent yields within 30 min, even which typically requires 24 h or longer reduce under uncatalyzed conditions. Several potentially reactive functionalities tolerated, and substituted cycloalkanones reduced diastereoselectively thermodynamic product. A deuterium labeling study 11B NMR analysis have been performed verify proposed hydroboration mechanism.
Язык: Английский
Процитировано
20
Organic & Biomolecular Chemistry, Год журнала: 2022, Номер 20(5), С. 1103 - 1111
Опубликована: Янв. 1, 2022
A Pd( ii ) complex catalysed hydroboration and reductive amination reaction of several aldehydes ketones are reported. DFT-based computational study the mechanism unravels dual role HBpin in accomplishing reaction.
Язык: Английский
Процитировано
17
European Journal of Inorganic Chemistry, Год журнала: 2022, Номер 2022(20)
Опубликована: Май 16, 2022
Abstract Two new examples of β ‐diketiminate or NacNac analogues, i. e ., conjugated bis‐guanidinate (CBG) stabilized low valent germanium chloride ( 1 ) and hydride 2 complexes, are reported. Deprotonation LH upon treatment with n ‐BuLi an in situ generated LLi further treated GeCl ⋅dioxane afforded LGeCl 79 % yield. Compound reacted source NaHBEt 3 toluene, Ge (II) 76 Both compounds were characterized by NMR mass spectroscopic methods. Further, catalyzed hydroboration cyanosilylation a wide range ketones have been investigated. Control reactions suggest occurred via insertion Ge−O/B−H bond metathesis pathways. It is worthy mentioning that, the case ketones, reducible groups such as alkene, alkyne, halide, ester, nitro, heterocycles untouched. Furthermore, compound was employed for reduction carbonate, formate, anhydride substrates technique.
Язык: Английский
Процитировано
16
European Journal of Inorganic Chemistry, Год журнала: 2022, Номер 2022(8)
Опубликована: Янв. 22, 2022
Abstract The N , N’ ‐chelated β ‐diketiminate analogue i. e ., conjugated bis‐guanidine (CBG) ligand L(3H) [L= {(ArHN)(ArN)−C=N−C=(NAr)(NHAr)}; Ar=2,6‐Et 2 ‐C 6 H 3 ], has been used to synthesize mono‐ and dinuclear Al(III) dimethyl complexes, [L(2H) AlMe ] ( 1) [L(H)(AlMe ) ). Compounds 1 are synthesized by deprotonation method using free appropriate stoichiometric amounts of structurally characterized a single‐crystal X‐ray diffraction technique. Moreover, the reaction compound with B(C F 5 afforded three‐coordinate aluminum methyl cation [L(2H)AlMe] + [MeB(C − in good yield. Compound was thermally stable multinuclear NMR spectroscopy. Furthermore, we demonstrated that catalyzed hydrosilylation carbonyls, alkenes, alkyne triethylsilane (HSiEt under solvent‐free conditions. We found catalyst is also effective for large‐scale reactions. Additionally, have shown benzaldehyde's intermolecular chemoselective over other reducible functional groups.
Язык: Английский
Процитировано
14
Chemistry - A European Journal, Год журнала: 2022, Номер 29(4)
Опубликована: Окт. 13, 2022
In this work, the molecular aluminium dihydride complex bearing an N, N'-chelated conjugated bis-guanidinate (CBG) ligand is used as a catalyst for reducing wide range of aryl and alkyl esters with good tolerance alkene (C=C), alkyne (C≡C), halides (Cl, Br, I F), nitrile (C≡N), nitro (NO2 ) functionalities. Further, we investigated catalytic application in C-O bond cleavage epoxides into corresponding branched Markovnikov ring-opening products. addition, chemoselective intermolecular reduction over other reducible functional groups, such amides alkenes, has been established. Intermediates are isolated characterized by NMR HRMS studies, which confirm probable cycles hydroboration epoxides.
Язык: Английский
Процитировано
13
Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(15), С. 2571 - 2575
Опубликована: Июнь 29, 2022
Abstract We describe a palladium‐catalyzed deoxygenative transfer hydrogenation of ketones using B 2 (OH) 4 as the sole additive. Deuterium labeling experiments (OD) show that incorporated protons originate exclusively from diboron reagent. Spectroscopic evidence implicates intermediacy borate ester. A variety aromatic can be deoxygenated this approach. magnified image
Язык: Английский
Процитировано
7