Bond-Forming Processes Enabled by Silicon-Masked Aryl- and Alkyl-Substituted Diazenes DOI
Lucie Finck, Martin Oestreich

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 15531 - 15539

Published: Nov. 7, 2023

Aryl- and alkyldiimides (R–N═NH with R = aryl or alkyl) are elusive intermediates of valuable synthetic use, as they assumed to be transient species in processes involving both carbon (with concomitant loss N2) nitrogen nucleophiles conservation the N═N moiety). The actual compounds fragile such not bench stable which is why have yet found attention deserve. Conversely, early contributions showed that stability parent diimide significantly increased by replacing hydrogen atom a silyl group, but applicability these silicon-protected aryl- alkyldiazenes has been far less explored, part due absence general procedures for their preparation. This Perspective provides an overview underexplored diazene chemistry witnessed considerable progress recent years highlights potential this motif range synthetically useful (catalytic) transformations. rediscovered silicon-masked diazenes constitute versatile platform possessing enhanced tamed reactivity comparison hydrogen-substituted diimides. Aryl, diazenyl, alkyl anionic key can selectively generated situ under Lewis base transition metal catalysis, giving rise novel approaches viable alternatives already existing methodologies.

Language: Английский

Advances and developments in transition metal-free benzylic C(sp3)–H activation/functionalization reactions DOI Creative Commons
Fatemeh Doraghi,

Shahab Kermaninia,

Elika Salehi Ghalehsefid

et al.

RSC Advances, Journal Year: 2025, Volume and Issue: 15(19), P. 14691 - 14716

Published: Jan. 1, 2025

Transition metal-free benzylic C(sp 3 )–H activation is a direct strategy for forming C–C and C–X bonds. This review highlights C–H activation/annulation or activation/functionalization of toluenes using non-metal catalysts promoters.

Language: Английский

Citations

0
Bond-Forming Processes Enabled by Silicon-Masked Aryl- and Alkyl-Substituted Diazenes DOI
Lucie Finck, Martin Oestreich

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(22), P. 15531 - 15539

Published: Nov. 7, 2023

Aryl- and alkyldiimides (R–N═NH with R = aryl or alkyl) are elusive intermediates of valuable synthetic use, as they assumed to be transient species in processes involving both carbon (with concomitant loss N2) nitrogen nucleophiles conservation the N═N moiety). The actual compounds fragile such not bench stable which is why have yet found attention deserve. Conversely, early contributions showed that stability parent diimide significantly increased by replacing hydrogen atom a silyl group, but applicability these silicon-protected aryl- alkyldiazenes has been far less explored, part due absence general procedures for their preparation. This Perspective provides an overview underexplored diazene chemistry witnessed considerable progress recent years highlights potential this motif range synthetically useful (catalytic) transformations. rediscovered silicon-masked diazenes constitute versatile platform possessing enhanced tamed reactivity comparison hydrogen-substituted diimides. Aryl, diazenyl, alkyl anionic key can selectively generated situ under Lewis base transition metal catalysis, giving rise novel approaches viable alternatives already existing methodologies.

Language: Английский

Citations

3