72137-22-5Relevant articles and documents
Hydroboration. 76. Hydroboration of Cyclic Dienes with Representative Hydroborating Agents
Brown, Herbert C.,Bhat, Krishna S.
, p. 445 - 449 (1986)
A detailed study was made of the hydroboration of cyclic dienes with representative hydroborating agents: borane-methyl sulfide (BMS), 9-borabicyclononane (9-BBN), disiamylborane (Sia2BH), dibromo-borane-methyl sulfide (Br2BH*SMe2), and dibromoborane (Br2BH). 1,4-Cyclohexadiene essentially undergoes monohydroboration with a stoichiometric amount of the representative hydroborating agents, whereas 1,5-cyclooctadiene gives the dihydroboration product predominantly.The rapid dimerization of 1,3-cyclopentadiene introduces a complication into its hydroboration.However, monomeric cyclopentadiene undergoes hydroboration primarily to the homoallylic derivative with little of the desired allylic product.Hydroboration of 1,3-cyclohexadiene with a stoichiometric amount of the hydroborating agent furnishes mainly the allylboranes, which upon treatment with acetaldehyde followed by oxidation, furnishes 1-(2-cyclohexenyl)-1-ethanol in good yield.Similary, hydroboration of 1,3-cycloheptadiene and 1,3-cyclooctadiene furnished dihydroborated products preferentially, with lower yields of the corresponding allylboranes, characterized as 1-(2-cycloheptenyl)-1-ethanol and 1-(2-cyclooctenyl)-1-ethanol, respectively, following reaction with acetaldehyde.
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Pearlman,B.A.
, p. 6398 - 6404 (1979)
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Tuning acylthiourea ligands in Ru(II) catalysts for altering the reactivity and chemoselectivity of transfer hydrogenation reactions, and synthesis of 3-isopropoxy-1H-indole through a new synthetic approach
Sathishkumar, Pushpanathan N.,Prabha, Padinhattath Sachind,Bhuvanesh, Nattamai S.P.,Karvembu, Ramasamy
, (2020/01/09)
Ru(II)-p-cymene complexes (1–3) containing picolyl based pseudo-acylthiourea ligands (L1-L3) were synthesized and characterized. The crystallographic study confirmed the molecular structures of all the ligands (L1-L3) and complex 3. The catalytic activity of the complexes was tested mainly towards TH of carbonyl compounds and nitroarenes. The influence of steric and electronic effects of the ligands on the chemoselectivity and reactivity were reported. The catalytic activity was enhanced and chemoselectivity was switched after tuning the ligands in the catalysts, compared to their corresponding unmodified Ru(II)-p-cymene complexes. The catalysis was extended to a broad range of substrates including some challenging systems like furfural, benzoylpyridine, benzoquinone, chromanone, etc. The strategy of tuning the bifunctional ligands in the catalysts for effective and selective catalysis worked nicely. Further, the catalysis was extended to one pot synthesis of 3-isopropoxyindole from 2-nitrocinnamaldehyde, the first synthetic route similar to Baeyer Emmerling indole synthesis. All the catalytic experiments exhibited high conversion and selectivity.
Ru-Photoredox-Catalyzed Decarboxylative Oxygenation of Aliphatic Carboxylic Acids through N-(acyloxy)phthalimide
Zheng, Chao,Wang, Yuting,Xu, Yangrui,Chen, Zhen,Chen, Guangying,Liang, Steven H.
, p. 4824 - 4827 (2018/08/24)
Decarboxylative aminoxylation of aliphatic carboxylic acid derivatives with (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) in the presence of ruthenium photoredox catalysis is reported. The key transformation entails a highly efficient photoredox catalytic cycle using Hantzsch ester as a reductant. The ensuing alkoxyamine can be readily converted to the corresponding alcohol in one pot, representing an alternative approach to access aliphatic alcohols under photoredox conditions.
