88682-29-5Relevant academic research and scientific papers
Diarylmethanols synthesis by nickel(II)-catalyzed addition of arylboronic acids to aryl aldehydes
Bie, Fusheng,Cao, Han,Cui, Haizhu,Li, Tang,Liu, Xuejing,Ma, Jie,Wang, Meng
supporting information, p. 248 - 253 (2020/04/24)
A practical procedure for the addition of arylboronic acids to aromatic aldehydes has been developed in the presence of NiCl2(PPh3)2/1,3-bis-(2,6-diisopropylphenyl)imidazolium chloride (IPr·HCl) system with good yield. Generally, electron-rich and-neutral aryl aldehydes showed excellent reactivity and provided desired products in high yields. This procedure will provide new way to the synthesis of diarylmethanols.
Deoxyfluorination with CuF2: Enabled by Using a Lewis Base Activating Group
Bode, Bela E.,Chabbra, Sonia,Champion, Sue,Dawson, Daniel M.,Sood, D. Eilidh,Sutherland, Andrew,Watson, Allan J. B.
supporting information, p. 8460 - 8463 (2020/04/10)
Deoxyfluorination is a primary method for the formation of C?F bonds. Bespoke reagents are commonly used because of issues associated with the low reactivity of metal fluorides. Reported here is the development of a simple strategy for deoxyfluorination, using first-row transition-metal fluorides, and it overcomes these limitations. Using CuF2 as an exemplar, activation of an O-alkylisourea adduct, formed in situ, allows effective nucleophilic fluoride transfer to a range of primary and secondary alcohols. Spectroscopic investigations have been used to probe the origin of the enhanced reactivity of CuF2. The utility of the process in enabling 18F-radiolabeling is also presented.
Chemoselective reduction of aldehydes: Via a combination of NaBH4 and acetylacetone
Sui, Guoqing,Lv, Qingyun,Song, Xiaoqing,Guo, Huihui,Dai, Jiatong,Ren, Li,Lee, Chi-Sing,Zhou, Wenming,Hao, Hong-Dong
, p. 15793 - 15796 (2019/10/19)
A bench-stable combination of NaBH4-acetylacetone was developed for the efficient chemoselective reduction of aldehydes in the presence of ketones. This method offers a useful synthetic protocol for distinguishing carbonyl reaction sites, and its synthetic utility is reflected by its moisture tolerance and high efficiency in a variety of complex settings.
Nickel-Catalyzed Addition of Aryl Bromides to Aldehydes to Form Hindered Secondary Alcohols
Garcia, Kevin J.,Gilbert, Michael M.,Weix, Daniel J.
supporting information, p. 1823 - 1827 (2019/02/14)
Transition-metal-catalyzed addition of aryl halides across carbonyls remains poorly developed, especially for aliphatic aldehydes and hindered substrate combinations. We report here that simple nickel complexes of bipyridine and PyBox can catalyze the addition of aryl halides to both aromatic and aliphatic aldehydes using zinc metal as the reducing agent. This convenient approach tolerates acidic functional groups that are not compatible with Grignard reactions, yet sterically hindered substrates still couple in high yield (33 examples, 70% average yield). Mechanistic studies show that an arylnickel, and not an arylzinc, adds efficiently to cyclohexanecarboxaldehyde, but only in the presence of a Lewis acid co-catalyst (ZnBr2).
An Efficient Ga(OTf)3/Isopropanol Catalytic System for Direct Reduction of Benzylic Alcohols
Sai, Masahiro
, p. 4330 - 4335 (2018/10/15)
This study aims to report the first gallium-catalyzed direct reduction of benzylic alcohols using isopropanol as a reductant. The reaction proceeds via gallium catalyst-assisted hydride transfer of the in situ-generated benzylic isopropyl ether. The method generates only water and acetone as byproducts and thus provides an atom-economic and environmentally friendly approach to the synthesis of di- and triarylmethanes, which are important substructures in various bioactive compounds and functional materials. (Figure presented.).
DTBB-catalysed lithiation of chlorinated benzylic chlorides, alcohols, thiols or amines
Gomez, Cecilia,Huerta, Fernando F.,Yus, Miguel
, p. 1853 - 1866 (2007/10/03)
The reaction of chlorinated benzyl chlorides (I) with an excess of lithium powder and a catalytic amount of DTBB (4 mol %) in the presence of different electrophiles [Pr(i)CHO, Bu(t)CHO, Et2CO, (CH2)5CO, PhCOMe, Me3/
Lanthanoids in Organic Synthesis. I. The Novel Reduction of Carboxylic Acids with Samarium Diiodide-Base System
Kamochi, Yasuko,Kudo, Tadahiro
, p. 3049 - 3054 (2007/10/02)
Aromatic and aliphatic carboxylic acids were rapidly reduced with samarium diiodide by the addition of base in the presence of protic solvent at room temperature to the corresponding alcohols.Sodium benzoate was similarly reduced with samarium diiodide in the presence of H2O in a good yield.In the similar reactions of benzoic acid derivatives bearing carboxyl, formyl, carbamoyl, methoxyl, and chloro groups, these functional groups were also reduced to the corresponding alcohol or amine derivatives.Interestingly, the carboxyl and formyl groups of benzoic acids were partly reduced into the methyl group.
CHEMOSELECTIVE REDUCTION OF ALDEHYDES WITH TETRA-n-BUTYLAMMONIUM TRIACETOXYBOROHYDRIDE
Nutaitis, Charles F.,Gribble, Gordon W.
, p. 4287 - 4290 (2007/10/02)
Aldehydes, but not ketones, are smoothly reduced to alcohols by tetra-n-butylammonium triacetoxyborohydride in refluxing benzene.
