- Regiodivergent Hydroborative Ring Opening of Epoxides via Selective C-O Bond Activation
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A magnesium-catalyzed regiodivergent C-O bond cleavage protocol is presented. Readily available magnesium catalysts achieve the selective hydroboration of a wide range of epoxides and oxetanes yielding secondary and tertiary alcohols in excellent yields and regioselectivities. Experimental mechanistic investigations and DFT calculations provide insight into the unexpected regiodivergence and explain the different mechanisms of the C-O bond activation and product formation.
- Magre, Marc,Paffenholz, Eva,Maity, Bholanath,Cavallo, Luigi,Rueping, Magnus
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supporting information
p. 14286 - 14294
(2020/09/15)
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- Controllable Intramolecular Unactivated C(sp3)-H Amination and Oxygenation of Carbamates
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Dual catalyst-controlled intramolecular unactivated C(sp3)-H amination and oxygenation of carbamates merging visible-light photocatalysis and earth-abundant transition metal catalysis have been reported. Useful amino alcohol and diol derivatives could be selectively obtained from readily available tertiary alcohol derivatives. The possible mechanisms have been proposed via a 1,5-HAT process followed by Lewis acid-controlled cyclization. The nickel and zinc catalysts inhibit the formation of oxygenation and amination products, respectively. An interesting phenomenon of chirality transfer is also observed.
- Guo, Qihang,Ren, Xiang,Lu, Zhan
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p. 880 - 884
(2019/05/16)
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- Direct construction of quaternary carbons from tertiary alcohols via photoredox-catalyzed fragmentation of tert-alkyl N-phthalimidoyl oxalates
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A convenient method for the direct construction of quaternary carbons from tertiary alcohols by visible-light photoredox coupling of tert-alkyl N-phthalimidoyl oxalate intermediates with electron-deficient alkenes is reported.
- Lackner, Gregory L.,Quasdorf, Kyle W.,Overman, Larry E.
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supporting information
p. 15342 - 15345
(2013/11/06)
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- REDUCTIVE DESULFONYLATION OF PHENYL SULFONES BY SAMARIUM(II) IODIDE-HEXAMETHYLPHOSPHORIC TRIAMIDE
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Samarium(II) iodide in tetrahydrofuran reductively desulfonylates phenyl sulfones in the presence of hexamethylphosphoric triamide.This transformation is illustrated here for ten substrates, which include secondary alicyclic, β-hydroxy, vicinal bis-, and α,β-unsaturated sulfones.
- Kuenzer, H.,Stahnke, M.,Sauer, G.,Wiechert, R.
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p. 1949 - 1952
(2007/10/02)
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