In an article, author is Li, Ting, once mentioned the application of 1113-38-8, Name is Ammonium oxalate, molecular formula is C2H8N2O4, molecular weight is 124.1, MDL number is MFCD00013308, category is benzisoxazole. Now introduce a scientific discovery about this category, Safety of Ammonium oxalate.
Mechanism and Origins of Product Selectivity of Au-Catalyzed Coupling Benzisoxazoles with Ynamides: A Computational Study
Au(I)-catalyzed coupling of benzisoxazoles and ynamides was recently reported to synthesize challenging indoloquinoline core structures. In this report, we employed DFT methods to elucidate the mechanistic details of this reaction. The results reveal that the catalytic cycle involves initial coupling of ynamide with benzisoxazole, simultaneous ring opening of the isoxazole unit and attack of the dimethoxybenzene (DMOB) unit to gold carbenoid, proton transfer from the DMOB group to hydroxyl group, thioether migration, ring closure, and proton transfer. The experimentally observed ligand-controlled product selectivity is reproduced well by the calculations. The product selectivity-determining step is the ring opening of the isoxazole unit. The flexible P(t-Bu)(2)(o-biphenyl) ligand facilitates the approach of the DMOB group to gold carbenoid, which brings about significant C-H/pi interactions in the transition state for ring opening, and thus leads to the indoloquinoline product. The rigid 1,3-bis(diisopropylphenyl)imidazol-2-ylidene ligand prefers keeping the DMOB group away from the gold carbenoid, which can cause strong orbital interaction in the transition state for ring opening, and thus results in indole product.
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Reference:
Benzisoxazole – Wikipedia,
,Benzisoxazole – an overview | ScienceDirect Topics