Ketenes and other cumulenes as reactive intermediates

AD Allen, TT Tidwell - Chemical Reviews, 2013 - ACS Publications
Reactive intermediates as recognized chemical entities date back for over a century, and
among the earliest examples were simple free radicals, as identified in 1879, when it was …

Transition metal-catalyzed C–H bond functionalization in multicomponent reactions: a tool toward molecular diversity

JP Wan, L Gan, Y Liu - Organic & Biomolecular Chemistry, 2017 - pubs.rsc.org
Transition metal-catalyzed C–H bond functionalization has numerous applications in
organic synthesis as a powerful type of bond transformation. In particular, the combination of …

Three-component visible-light-induced palladium-catalyzed 1, 2-alkyl carbamoylation/cyanation of alkenes

X Jia, Z Zhang, V Gevorgyan - ACS catalysis, 2021 - ACS Publications
A mild visible-light-induced Pd-catalyzed one-pot three-component alkyl-carbamoylation
and cyanation of alkenes was developed. This general transformation, which proceeds via …

Ketenimines Generated from Ynamides: Versatile Building Blocks for Nitrogen‐Containing Scaffolds

RH Dodd, K Cariou - Chemistry–A European Journal, 2018 - Wiley Online Library
Using ynamides as readily available starting materials, a single step can generate highly
reactive ketenimines, which can then undergo a variety of transformations. The choice of the …

Palladium (II)-catalyzed cross-coupling of diazo compounds and isocyanides to access ketenimines

Z Liu, S Cao, J Wu, G Zanoni, P Sivaguru, X Bi - ACS Catalysis, 2020 - ACS Publications
Diazo compounds and isocyanides are reactive functionalities and valuable building blocks
commonly utilized in organic synthesis. Their cross-coupling for the synthesis of useful …

Optimization of fluorinated phenyl azides as universal photocrosslinkers for semiconducting polymers

ZS Tan, Z Jamal, DWY Teo, HC Ko, ZL Seah… - Nature …, 2024 - nature.com
Fluorinated phenyl azides (FPA) enable photo-structuring of π-conjugated polymer films for
electronic device applications. Despite their potential, FPAs have faced limitations regarding …

Ketenimines from Isocyanides and Allyl Carbonates: Palladium‐Catalyzed Synthesis of β, γ‐Unsaturated Amides and Tetrazoles

G Qiu, M Mamboury, Q Wang, J Zhu - Angewandte Chemie, 2016 - Wiley Online Library
The reaction of allyl ethyl carbonates with isocyanides in the presence of a catalytic amount
of Pd (OAc) 2 provided ketenimines through β‐hydride elimination of the allyl …

Iron‐Catalysed Carbene Transfer to Isocyanides as a Platform for Heterocycle Synthesis

TR Roose, HD Preschel… - … A European Journal, 2023 - Wiley Online Library
An iron‐catalysed carbene transfer reaction of diazo compounds to isocyanides has been
developed. The resulting ketenimines are trapped in situ with various bisnucleophiles to …

Cu-Catalyzed Aerobic Oxidative Three-Component Coupling Route to N-Sulfonyl Amidines via an Ynamine Intermediate

J Kim, SS Stahl - The Journal of Organic Chemistry, 2015 - ACS Publications
Cu-catalyzed aerobic oxidative three-component coupling of a terminal alkyne, secondary
amine, and sulfonamide enables efficient synthesis of amidines. The use of Cu (OTf) 2 (5 …

Aza-Wolff rearrangement of N-fluoroalkyl triazoles to ketenimines

A Kubíčková, A Markos, S Voltrová… - Organic Chemistry …, 2023 - pubs.rsc.org
N-Fluoroalkylated 1, 2, 3-triazoles underwent a microwave-heating-assisted ring opening,
nitrogen molecule elimination and concomitant group rearrangement to form isolable N …