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Direct Calpha-heteroarylation of structurally diverse ethers: Via a mild N -hydroxysuccinimide mediated cross-dehydrogenative coupling reaction
An important challenge in the Calpha-heteroarylation of ethers is the requirement of a large excess amount of ethers (that are used as solvents in many cases) to achieve effective transformations. This drawback has significantly restricted the Calpha-heteroarylation of ethers to the use of simple and easily accessible ether substrates. To overcome this limitation, a new, efficient, N-hydroxysuccinimide (NHS) mediated, mild and metal-free CDC strategy for the direct Calpha-heteroarylation of diverse ethers has been developed. Different to our previous benzaldehyde mediated photoredox Calpha-heteroarylation, we have identified NHS as a new and efficient mediator without using light. A distinct non-photoredox engaged hydrogen-atom-transfer (HAT) mechanism that used a nitrogen-centered radical cation produced from NHS is initially revealed. Notably, only 5-10 equivalents of ethers as coupling partners are used, which allows for structurally diverse and complex ethers to engage in this process, to create highly medicinally relevant Calpha-heteroarylated ethers. Furthermore, more structurally diverse heterocyclics can serve as reactants for this process.
Note that a catalyst decreases the activation energy for both the forward and the reverse reactions and hence accelerates both the forward and the reverse reactions.name: Tetrahydrofurfuryl Acetate, you can also check out more blogs about637-64-9
Reference£º
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem