144498-52-2

Upstream product

• 24566-90-3 octyl chloromethyl ether 
• 3757-88-8 tributylstannylethynylbenzene 
• 111-87-5 octanol 
• 1327239-36-0 N-methyl-N-(octyloxymethoxy)acetamide 
• 88738-43-6 methoxymethyl octyl ether 

Relevant academic research and scientific papers

Expanded substrate scope and improved reactivity of ether-forming cross-coupling reactions of organotrifluoroborates and acetals

Mixed acetals and organotrifluoroborates undergo BF3· OEt2-promoted cross-couplings to give dialkyl ethers under simple, mild conditions. A survey of reaction partners identified a hydroxamate leaving group that improves the regioselectivity and product yield in the BF 3·OEt2-promoted coupling reaction of mixed acetals and potassium alkynyl-, alkenyl-, aryl- and heteroaryltrifluoroborates to access substituted dialkyl ethers. This leaving group enables the reaction to proceed rapidly under mild conditions (0 °C, 5-60 min) and permits reactions with electron-deficient potassium aryltrifluoroborates that are less reactive with other acetal substrates. A study of the reaction mechanism and characterization of key intermediates by NMR spectroscopy and X-ray crystallography identified a role for the hydroxamate moiety as a reversible leaving group that serves to stabilize the key oxocarbenium intermediate and the need for a slight excess of organodifluoroborane to serve as a catalyst. A secondary role for the boron nucleophile as an activating ligand was also considered. These studies provide the basis for a general class of reagents that lead to dialkyl ethers by a simple, predictable cross-coupling reaction.

Synthesis of dialkyl ethers from organotrifluoroborates and acetals

(Chemical Equation Presented) The formation of ethers by C-O bond formation under harsh basic or acidic conditions is an entrenched synthetic disconnection in organic chemistry. We report a strategic alternative that involves the BF3?OEt2

A new method of synthesis for propargylic amines and ethers via benzotriazole derivatives using sodium dialkynyldiethylaluminates

1-(α-Aminoalkyl)benzotriazoles react with sodium dialkynyldiethylaluminates to give propargylic amines in excellent yields, including unsubstituted N,N-dialkyl propargylamines, which are difficult to obtain from lithium acetylide. The reaction of α-benzotriazolyl alkyl ethers and sodium dialkynyldiethylaluminate in the presence of zinc iodide also gives propargylic ethers in excellent yields. Unsubstituted propargyl ethers are prepared via the desilylation of trimethylsilylpropargyl ethers.

Palladium catalyzed cross-coupling and tandem cyclization-coupling of α-halo(thio)ethers with organotins

Pd(0) mediates the cross-coupling of organotins with a variety of α-haloethers/thioethers in moderate-good yields whereas an α-chloroacetoxyalkene failed to react. Tandem cyclization-coupling of the alkyl-palladium intermediate affords novel access to heterocycles.