Ni‐Catalyzed Cyanation of Allylic Alcohols with Formamide as the Cyano Source

Deng, Lin-Fang; Cheng, Jian; Chen, Junjia; Yang, Luo

doi:10.1002/ejoc.202200339

Eur J Org Chem

2022

DOI: 10.1002/ejoc.202200339

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Ni‐Catalyzed Cyanation of Allylic Alcohols with Formamide as the Cyano Source

Lin-Fang Deng

Jian Cheng

Junjia Chen

et al.

Abstract: Formamide as the safe cyano source! A Ni-catalyzed cyanation of unactivated allylic alcohols and formamide to provide various α,β-unsaturated nitriles was developed by generating the cyano unit in situ from safe and readily available formamide.

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The effect of tethered bi-naphthyls on visible-light promoted alkene-alkene [2 + 2] cycloadditions

Hoch,

Sparascio,

Cerveri

et al. 2024

Photochem Photobiol Sci

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Dispersion interactions are ubiquitous weak interactions that can play a role in many chemical events. Tailor-made catalysts and additives can lead to more selective reactions by properly exploiting dispersion interactions. Although radical-π dispersion interactions are known to have an important stabilizing role, this concept has been so far overlooked in synthetic photochemistry. We recently proved that similar dispersion interactions can play a profound impact on several reactions involving an energy transfer step. We present herein a study on the co-catalytic effect of tethered bi-naphthyl derivatives on the visible-light-promoted alkene-alkene [2 + 2] cycloaddition. A library of tethered bi-naphthyl derivatives was prepared in order to evaluate the impact of the tether on the efficiency of the prototypical [2 + 2] cycloaddition. The best performing additives showed a dramatic effect on the efficiency of the cyclization, and a rationalization of their relative efficiency was carried out through DFT modeling. The best co-catalyst allowed one to isolate desired products in good to excellent yields even employing several challenging substrates. These results offer new tools to devise optimized [2 + 2] photocycloaddition methods and provide valuable information for the design of organic co-catalyst that can boost photochemical reactions by exploiting dispersion interactions. Graphical abstract

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The effect of tethered bi-naphthyls on visible-light promoted alkene-alkene [2 + 2] cycloadditions

Hoch,

Sparascio,

Cerveri

et al. 2024

Photochem Photobiol Sci

View full text Add to dashboard Cite

show abstract

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Ni‐Catalyzed Cyanation of Allylic Alcohols with Formamide as the Cyano Source

Abstract: Formamide as the safe cyano source! A Ni-catalyzed cyanation of unactivated allylic alcohols and formamide to provide various α,β-unsaturated nitriles was developed by generating the cyano unit in situ from safe and readily available formamide.

Cited by 1 publication

References 42 publications

The effect of tethered bi-naphthyls on visible-light promoted alkene-alkene [2 + 2] cycloadditions

The effect of tethered bi-naphthyls on visible-light promoted alkene-alkene [2 + 2] cycloadditions

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