In an article, author is Kaithal, Akash, once mentioned the application of 535-11-5, SDS of cas: 535-11-5, Name is Ethyl 2-bromopropionate, molecular formula is C5H9BrO2, molecular weight is 181.0278, MDL number is MFCD00000144, category is esters-buliding-blocks. Now introduce a scientific discovery about this category.
Ruthenium-Catalyzed Selective Hydroboronolysis of Ethers
A ruthenium-catalyzed reaction of HBpin with substituted organic ethers leads to the activation of C-O bonds, resulting in the formation of alkanes and boronate esters via hydroboronolysis. A ruthenium precatalyst, [Ru (p-cymene)Cl](2)Cl-2 (1), is employed, and the reactions proceed under neat conditions at 135 degrees C and atmospheric pressure (ca. 1.5 bar at 135 degrees C). Unsymmetrical dibenzyl ethers undergo selective hydroboronolysis on relatively electron-poor C-O bonds. In arylbenzyl or alkylbenzyl ethers, C-O bond cleavage occurs selectively on C-Bn-OR bonds (Bn = benzyl); in alkylmethyl ethers, selective deconstruction of C-Me-OR bonds leads to the formation of alkylboronate esters and methane. Cyclic ethers are also amenable to catalytic hydroboronolysis. Mechanistic studies indicated the immediate in situ formation of a mono-hydridobridged dinuclear ruthenium complex [{(eta(6)-p-cymene)RuCl}(2)(mu-H-mu-Cl)] (2), which is highly active for hydroboronolysis of ethers. Over time, the dinuclear species decompose to produce ruthenium nanoparticles that are also active for this transformation. Using this catalytic system, hydroboronolysis could be applied effectively to a very large scope of ethers, demonstrating its great potential to cleave C-O bonds in ethers as an alternative to traditional hydrogenolysis.
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