50878-44-9Relevant academic research and scientific papers
Formation by SRN1 reactions and 1H N.M.R. properties of sterically encumbered 2,4,6-triaIkyIphenyl p-nitrobenzyl sulfides
Look, Kai,Norris, Robert K.
, p. 1077 - 1083 (1999)
Sterically hindered p-nitrobenzylic chlorides (1) and (2) react with the sodium salts of 2,4,6-trialkylbenzenethiols (3a)-(5a) by the SRN1 reaction to give good yields of the corresponding p-nitrobenzylic aryl sulfides (6)-(10). For example, th
Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling
Kim, Byoungmoo,Chinn, Alex J.,Fandrick, Daniel R.,Senanayake, Chris H.,Singer, Robert A.,Miller, Scott J.
supporting information, p. 7939 - 7945 (2016/07/07)
We report the development of a new class of guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields were achieved in the long-range asymmetric cross-coupling (up to 93:7 er and 76% yield) between aryl bromides and malonates. Our mechanistic studies suggest that distal stereocontrol is achieved through a Cs-bridged interaction between the Lewis-basic C-terminal carboxylate of the peptides with the distal arene of the substrate.
