1415029-93-4Relevant articles and documents
Synthesis of aryl allyl alkynes via reaction with allyl amine and aryl alkynoic acids through decarboxylation
Lee, Jieun,Nam, Kye Chun,Lee, Sunwoo
supporting information, p. 1008 - 1015 (2020/03/04)
Allyl alkynoic esters were synthesized by the reaction of allyl amines and alkynoic acids via deaminative esterification. The reaction of allyl alkynoic esters with Pd(dba)2 and Xantphos in digylme at 110 °C for 12 h afforded the desired decarb
Gold- or Indium-Catalyzed Cross-Coupling of Bromoalkynes with Allylsilanes through a Concealed Rearrangement
De Orbe, M. Elena,Zanini, Margherita,Quinonero, Ophélie,Echavarren, Antonio M.
, p. 7817 - 7822 (2019/08/20)
The gold(I)-catalyzed reaction of bromoalkynes with allylsilanes gives 1,4-enynes in a formal cross-coupling reaction. Mechanistic studies revealed the involvement of gold(I) vinylidenes or vinylidenephenonium gold(I) cations depending on the substituent on the bromoalkyne. In the case of bromo arylalkynes, the vinylidenephenonium gold(I) cations lead to 1,4-enynes via a 1,2-aryl rearrangement. The same reactivity has been observed in the presence of InBr3
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.