99464-29-6Relevant academic research and scientific papers
Redox-Activated Amines in C(sp3)-C(sp) and C(sp3)-C(sp2) Bond Formation Enabled by Metal-Free Photoredox Catalysis
Ociepa, Micha,Turkowska, Joanna,Gryko, Dorota
, p. 11362 - 11367 (2018/11/23)
The amino group represents one of the most prevalent structural motifs in organic chemistry. Therefore, application of amines as alkylating agents in synthesis is highly compelling. Herein, we present a metal-free photoredox strategy for the formation of C(sp3)-C(sp) and C(sp3)-C(sp2) bonds from redox-activated primary amine derivatives. The developed reaction of 2,4,6-triphenylpyridinium salts with alkynyl p-tolylsulfones, leading to functionalized alkynes, is easily scalable and offers broad substrate scope, high chemoselectivity, and mild conditions. Its potential is also highlighted by diversification of complex molecular scaffolds. Additionally, the approach is also suitable for synthesis of (E)-alkenes from vinyl phenyl sulfones. Mechanistic studies contribute to the elucidation of unexpected differences in reactivity of primary and secondary alkyl substituted pyridinium salts.
PALLADIUM-CATALYZED REGIO- AND STEREOSELECTIVE DESULFONYLATION OF ALLYLIC SULFONES WITH LiHBEt3. APPLICATION TO THE SYNTHESIS OF SQUALENE
Mohri, Mitsunobu,Kinoshita, Hideki,Inomata, Katsuhiko,Kotake, Hiroshi
, p. 451 - 454 (2007/10/02)
Allylic p-tolyl sulfones were easily desulfonylated to the corresponding alkenes by LiHBEt3 in the presence of a catalytic amount of under mild conditions with the preservation of the original stereochemistry.This reaction was successfully applied to the synthesis of squalene.
A CONVENIENT METHOD FOR THE SYNTHESIS OF HOMOALLYL ALCOHOL USING A NEW DESULFONYLATION METHOD
Kotake, Hiroshi,Yamamoto, Taku,Kinoshita, Hideki
, p. 1331 - 1334 (2007/10/02)
2-Tosyl homoallyl alcohol obtained by the reaction of allylic p-tolyl sulfone with aldehyde was found to be easily desulfonylated to homoallyl alcohol by the use of Pd(PPh3)4 as a catalyst and hydride ion as a nucleophile, without any side reactions.
