68986-70-9

Upstream product

• 14246-16-3 trimethyl(oct-1-yloxy)silane 
• 108-94-1 cyclohexanone 
• 111-87-5 octanol 
• 110-82-7 cyclohexane 

Downstream Products

• 111-65-9 octane 
• 110-82-7 cyclohexane 
• 14246-16-3 trimethyl(oct-1-yloxy)silane 

Relevant academic research and scientific papers

Cobalt-Catalyzed Secondary Alkylation of Arenes and Olefins with Alkyl Ethers through the Cleavage of C(sp2)-H and C(sp3)-O Bonds

A novel cobalt-catalyzed C-H alkylation of arenes and olefins is achieved with (pyridin-2-yl)isopropyl amine as an N,N-bidentate directing group. Different linear, branched, and cyclic alkyl ethers were used as practical secondary alkylating reagents through cleavage of C(sp3)-O bond, providing an efficient approach to the synthesis of verstile o-alkylated arylamides and tetrasubstituted acrylamides. Mechanistic studies indicate that cleavage of the inert C(sp3)-O bond involves a cobalt-promoted radical process and that cleavage of the inert C(sp2)-H bond by a cobalt catalyst is a rate-limiting step.

Synthesis of ethers from carbonyl compounds by reductive etherification catalyzed by iron(III) and silyl chloride

A simple iron- and silyl chloride catalyzed method for the preparation of symmetrical and nonsymmetrical ethers is presented. Various aldehydes and ketones were reductively etherified by using triethylsilane as a reducing agent in the presence of 2 mol% of iron(III) oxo acetate and 8 mol% of chloro(trimethyl)silane. The reactions can be carried out at ambient temperatures and pressures with ethyl acetate as the solvent.

CATALYTIC C-H BOND ACTIVATION FOR THE SYNTHESIS OF ETHERS AND THIOETHERS

Disclosed is a method for the transition metal-mediated oxidation of C-H bonds to form C-0 or C-S bonds. The methods are useful for the formation of ethers (R-OR') from alcohols, R'OH, and sp3 -hybridized C-H bonds in substrates, R-H. Aryl or heteroaryl acetates may also be used for C-H to C-OAr bond formation. The methods are also useful in the preparation of C-S bonds from acetyl-protected thiols, MeC(0)SR, and disulfides, RSSR. Advantageously, the methods minimize reaction steps, the handling of oxidized intermediates, and environmental impact.

Triflic acid catalyzed reductive coupling reactions of carbonyl compounds with O-, S-, and N-nucleophiles

Highly efficient metal-free reductive coupling reactions of aldehydes and ketones with a range of nucleophiles in the presence of triflic acid (1-5 mol %) as the catalyst are presented. The reactions can be performed at ambient temperature without exclusion of moisture or air. A range of symmetrical and unsymmetrical ethers were obtained by this method in high yields and short reaction times. For the first time, the influence of additional functionalization has been studied. Furthermore, the formation of thioethers from ketones (by addition of unmodified thiols) and of sulfonamides from either aldehydes or ketones has been achieved under catalytic conditions.

Catalytic reductive etherification of ketones with alcohols at ambient hydrogen pressure: A practical, waste-minimized synthesis of dialkyl ethers

A heterogeneous platinum catalyst was found to efficiently mediate the reductive etherification of ketones at ambient hydrogen pressure. In this environmentally benign transformation, water is released as the only by-product, and this is trapped with molecular sieves. The preparative utility of the new reaction protocol is demonstrated by the synthesis of ten unsymmetrical ethers from the corresponding ketones and primary or secondary alcohols. Georg Thieme Verlag Stuttgart.

Cu(OTf)2-catalyzed Et3SiH-reductive etherification of various carbonyl compounds with trimethylsilyl ethers

A triethylsilane-reductive etherification of the trimethylsilyl ethers with a variety of carbonyl compounds in good yields at room temperature employing 0.5 mol% Cu(OTf)2 as an extremely efficient catalyst is described here.

General Ether Synthesis under Mild Acid-Free Conditions. Trimethylsilyl Iodide Catalyzed Reductive Coupling of Carbonyl Compounds with Trialkylsilanes to Symmetrical Ethers and Reductive Condensation with Alkoxysilanes to Unsymmetrical Ethers

Facile synthesis of symmetrical ethers is achieved by either trimethylsilyl triflate or trimethylsilyl iodide catalyzed reductive coupling of carbonyl compounds (aldehydes and ketones) with trialkylsilanes.The method was also extended to the trimethylsilyl iodide catalyzed preparation of unsymmetrical ethers by reductive condensation (of carbonyl compounds) with alkoxysilanes.The scope and limitations of the reactions are discussed with emphasis on diastereoselectivity.