Catalytic asymmetric [4+1] spiroannulation of α-bromo-β-naphthols with azoalkenes by an electrophilic dearomatization/SRN1-debromination approach was written by Bai, Lu;Luo, Xin;Ge, Yicong;Wang, Hui;Liu, Jingjing;Wang, Yaoyu;Luan, Xinjun. And the article was included in CCS Chemistry in 2022.Recommanded Product: Copper(II) trifluoromethanesulfonate This article mentions the following:
An enantioselective [4+1]-spiroannulation of α-bromo-β-naphthols with azoalkenes has been developed for the one-step construction of a new class of pyrazoline-based spirocyclic mols. Using chiral Cu(II)/Box catalysts, asym. induction was achieved with high levels of enantioselectivity [up to 99:1 enantiomeric ratio (er)]. Notably, α-chloro- and α-iodo-substituted β-naphthols were also tolerated by this reaction. Mechanistic studies disclosed that this process was triggered by electrophile-facilitated dearomatization of α-bromo-β-naphthols and followed by the debromination via SRN1-substitution with an in situ-formed N-nucleophile. The chiral copper(II)-species, bound with azoalkene moiety, was assumed to control the enantio-discrimination over the naphthoxy C-radical that was generated from the debromination step. Moreover, the potential utility of this protocol was greatly amplified by the derivatization of spirocyclic products through oxidative dearomatization of the other aromatic ring in the naphthyl fragment, providing a rather attractive route for the rapid generation of synthetically more valuable doubly dearomatized architectures. In the experiment, the researchers used many compounds, for example, Copper(II) trifluoromethanesulfonate (cas: 34946-82-2Recommanded Product: Copper(II) trifluoromethanesulfonate).
Copper(II) trifluoromethanesulfonate (cas: 34946-82-2) belongs to copper catalysts. The applications of Copper-based nanoparticles have received great attention due to the earth-abundant, low toxicity and inexpensive. Copper nanoparticles can also catalyze the coupling reaction of nitrogen-containing nucleophiles, phenols, thiols, xanthogenates, selenium ruthenium nucleophiles and the like.Recommanded Product: Copper(II) trifluoromethanesulfonate
Referemce:
Copper catalysis in organic synthesis – NCBI,
Special Issue “Fundamentals and Applications of Copper-Based Catalysts”