850175-21-2Relevant academic research and scientific papers
Palladium-Catalyzed γ-C(sp3)?H Arylation of Thiols by a Detachable Protecting/Directing Group
Jin, Likun,Wang, Jianchun,Dong, Guangbin
supporting information, p. 12352 - 12355 (2018/09/18)
Reported herein is a palladium-catalyzed, directed γ-C(sp3)?H arylation of protected thiols. The key is to utilize Michael acceptors as a dual reagent to install a protecting/directing group on thiols by a thiol-Michael click reaction, and remove it later under basic conditions. The C?H arylation proceeds with high functional-group tolerance and the deprotected thiols can be further transformed into other sulfur-containing compounds. This unique mode of activation could open the door for site-selective functionalization of thiols or other sulfur-containing compounds at unactivated positions.
Remarkably mild and simple preparation of sulfenate anions from β-sulfinylesters: A new route to enantioenriched sulfoxides
Caupene, Caroline,Boudou, Cedric,Perrio, Stephane,Metzner, Patrick
, p. 2812 - 2815 (2007/10/03)
(Chemical Equation Presented) A general, efficient, and experimentally simple method for the generation of sulfenate salts has been developed using β-sulfmylesters as substrates. The process is based on a retro-Michael reaction, initiated by deprotonation at low temperature. Upon treatment with alkyl halides, the liberated sulfenates are subsequently converted into sulfoxides in good to excellent yield. Extension of the methodology to an unprecedented access to nonracemic sulfoxides by introduction of an enantiopure ligand, (-)-sparteine, is also described.
