16222-10-9Relevant articles and documents
Terpene ligands as the basis of catalytic systems for the asymmetric oxidation of phenylphenacyl sulfide
Kuchin,Ashikhmina,Rubtsova,Dvornikova
, p. 877 - 883 (2010)
Terpene ligands (1S,2S,5S)-3-[{2-[(2-hydroxybenzylidene)amino]ethyl}imino]- 2,6,6-trimethylbicyclo[3.1.1.]heptane-2-ol and 3-({2-[(2-hydroxy-2,6,6- trimethylbicyclo[3.1.1.]hept-3-ilidene)amino]ethyl}imino)-2,6, 6-trimethylbicyclo[3.1.1.]heptane-2-ol have
RuCl2(PPh3)3: A new catalyst for diazocarbonyl insertions into heteroatom-hydrogen bonds
Sengupta, Saumitra,Das, Debasis,Sen Sarma, Debarati
, p. 8815 - 8818 (1996)
The first ever use of RuCl2(PPh3)3 as a catalyst for diazoketone insertions into heteroatom-hydrogen bonds is described.
Steric-Free Bioorthogonal Labeling of Acetylation Substrates Based on a Fluorine-Thiol Displacement Reaction
Lyu, Zhigang,Zhao, Yue,Buuh, Zakey Yusuf,Gorman, Nicole,Goldman, Aaron R.,Islam, Md Shafiqul,Tang, Hsin-Yao,Wang, Rongsheng E.
, p. 1341 - 1347 (2021/02/01)
We have developed a novel bioorthogonal reaction that can selectively displace fluorine substitutions alpha to amide bonds. This fluorine-thiol displacement reaction (FTDR) allows for fluorinated cofactors or precursors to be utilized as chemical reporters, hijacking acetyltransferase-mediated acetylation both in vitro and in live cells, which cannot be achieved with azide- or alkyne-based chemical reporters. The fluoroacetamide labels can be further converted to biotin or fluorophore tags using FTDR, enabling the general detection and imaging of acetyl substrates. This strategy may lead to a steric-free labeling platform for substrate proteins, expanding our chemical toolbox for functional annotation of post-translational modifications in a systematic manner.
Competition Between Cα-S and Cα-Cβ Bond Cleavage in β-Hydroxysulfoxides Cation Radicals Generated by Photoinduced Electron Transfer?
Lapi, Andrea,D'Alfonso, Claudio,Del Giacco, Tiziana,Lanzalunga, Osvaldo
, p. 1310 - 1321 (2021/06/07)
A kinetic and product study of the 3-cyano-N-methyl-quinolinium photoinduced monoelectronic oxidation of a series of β-hydroxysulfoxides has been carried out to investigate the competition between Cα-S and Cα-Cβ bond cleavage within the corresponding cation radicals. Laser flash photolysis experiments unequivocally established the formation of sulfoxide cation radicals showing their absorption band (λmax ≈ 520?nm) and that of 3-CN-NMQ? (λmax ≈ 390?nm). Steady-state photolysis experiments suggest that, in contrast to what previously observed for alkyl phenyl sulfoxide cation radicals that exclusively undergo Cα-S bond cleavage, the presence of a β-hydroxy group makes, in some cases, the Cα-Cβ scission competitive. The factors governing this competition seem to depend on the relative stability of the fragments formed from the two bond scissions. Substitution of the β-OH group with -OMe did not dramatically change the reactivity pattern of the cation radicals thus suggesting that the observed favorable effect of the hydroxy group on the Cα-Cβ bond cleavage mainly resides on its capability to stabilize the carbocation formed upon this scission.
Air-Induced Disulfenylation of Alkenes: Facile Synthesis of Vicinal Dithioethers
Chen, Danyao,Chen, Qian,Huang, Yuanting,Ou, Yingcong,Yan, Y.,Yu, Guodian
supporting information, p. 83 - 86 (2019/12/30)
A novel disulfenylation of alkenes with thiophenols and their corresponding disulfides by using air as the oxidant has been achieved. This transformation provides a facile and practical protocol for the synthesis of vicinal dithioethers under mild conditions.
