A plant leaves-derived carbon material doped with two metals and preparation and use thereof are provided, the carbon material prepared by carbonizing, in an inert atmosphere, plant leaves which have absorbed ions of two metals M1 and M2. The metal M1 is Co, Mn, or Fe. The metal M2 is Ni, Cu, or Zn. The carbon material can be used as an efficient, green, and safe catalyst for the selective oxidation of cycloalkanes to produce cycloalkanols and cycloalkanones, and enable an increased selectivity of the target products (thus less by-products), a low yield of cycloalkyl peroxides, reduced reaction temperature, low environmental impact, and safe production.

A plant leaves-derived carbon material doped with two metals and preparation and use thereof are provided, the carbon material prepared by carbonizing, in an inert atmosphere, plant leaves which have absorbed ions of two metals M1 and M2. The metal M1 is Co, Mn, or Fe. The metal M2 is Ni, Cu, or Zn. The carbon material can be used as an efficient, green, and safe catalyst for the selective oxidation of cycloalkanes to produce cycloalkanols and cycloalkanones, and enable an increased selectivity of the target products (thus less by-products), a low yield of cycloalkyl peroxides, reduced reaction temperature, low environmental impact, and safe production.

The present invention concerns a method of oxidizing a cycloalkane to form a product mixture containing a corresponding alcohol and ketone, said method comprising contacting a cycloalkane with an oxidant agent in the presence of catalytic effective amount of metal triflates or metal triflimidates catalysts.

The present invention concerns a method of oxidizing a cycloalkane to form a product mixture containing a corresponding alcohol and ketone, said method comprising contacting a cycloalkane with an oxidant agent in the presence of catalytic effective amount of metal triflates or metal triflimidates catalysts.

The present invention discloses a new class of trans-cyclooctenes (TCOs), “a-TCOs,” that are prepared in high yield via stereocontrolled 1,2-additions of nucleophiles to trans-cyclooct-4-enone, which itself was prepared on large scale in two steps from 1,5-cyclooctadiene. Computational transition state models rationalize the diastereoselectivity of 1,2-additions to deliver a-TCO products, which were also shown to be more reactive than standard TCOs and less hydrophobic than even a trans-oxocene analog. Illustrating the favorable physicochemical properties of a-TCOs, a fluorescent TAMRA derivative in live HeLa cells was shown to be cell-permeable through intracellular Diels-Alder chemistry and to washout more rapidly than other TCOs.

The present invention discloses a new class of trans-cyclooctenes (TCOs), “a-TCOs,” that are prepared in high yield via stereocontrolled 1,2-additions of nucleophiles to trans-cyclooct-4-enone, which itself was prepared on large scale in two steps from 1,5-cyclooctadiene. Computational transition state models rationalize the diastereoselectivity of 1,2-additions to deliver a-TCO products, which were also shown to be more reactive than standard TCOs and less hydrophobic than even a trans-oxocene analog. Illustrating the favorable physicochemical properties of a-TCOs, a fluorescent TAMRA derivative in live HeLa cells was shown to be cell-permeable through intracellular Diels-Alder chemistry and to washout more rapidly than other TCOs.

The present disclosure provides bioorthogonal linkers and reagents, including trans-cyclooctene (TCO)- and tetrazine (Tz)-containing compounds. In a general aspect, the present disclosure provides reagents, conjugates, and bioactive molecules containing a trans-cyclooctene (TCO) fragment. Examples of TCO fragments include: Formulae (I) and (II).

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Disclosed herein are reaction compositions comprising an oxidation catalyst, a solvent, and a substrate that is dissolved in the solvent. The oxidation catalyst comprises a metal ion complexed with an -keto acid and a tridentate N,N,O-ligand. Also disclosed herein are methods for oxidizing a CH bond of a molecule, the methods comprising contacting the molecule with a metal complex comprising a metal ion complexed with a tridentate N,N,O-ligand in the presence of an -keto acid and a solvent. In some embodiments, the oxidation catalyst or metal complex is linked to a solid support.

Disclosed herein are reaction compositions comprising an oxidation catalyst, a solvent, and a substrate that is dissolved in the solvent. The oxidation catalyst comprises a metal ion complexed with an -keto acid and a tridentate N,N,O-ligand. Also disclosed herein are methods for oxidizing a CH bond of a molecule, the methods comprising contacting the molecule with a metal complex comprising a metal ion complexed with a tridentate N,N,O-ligand in the presence of an -keto acid and a solvent. In some embodiments, the oxidation catalyst or metal complex is linked to a solid support.

The present disclosure is directed to novel methods of oxidizing hydrocarbons, particularly terpenes, using ozone, compounds made according to said methods, and compositions comprising said compounds.