35822-50-5Relevant articles and documents
A visible-light photocatalytic thiolation of aryl, heteroaryl and vinyl iodides
Czyz,Weragoda,Monaghan,Connell,Brzozowski,Scully,Burton,Lupton,Polyzos
supporting information, p. 1543 - 1551 (2018/03/08)
The general catalytic synthesis of aryl and vinyl thioethers from readily available halides remains a challenge. Herein we report a unified method for the thiolation of aryl and vinyl iodides with dialkyl disulfides using visible light photoredox catalysis. A range of thioether products bearing diverse functional groups can be accessed in high yield and with excellent chemoselectivity. We demonstrate the versatility of this method through the expedient synthesis of a family of thioether-rich natural products. A detailed investigation of the photocatalytic mechanism is presented from both steady-state and time-resolved luminescent quenching as well as transient absorption spectroscopy experiments.
One-pot synthesis of alkyl styryl sulfides free from transition metal/ligand catalyst and thiols
Heredia, Adrian A.,Penenory, Alicia B.
, p. 991 - 997 (2013/03/14)
A new protocol for the one-pot synthesis of styryl alkyl sulfides was developed. This methodology involves the in situ generation of thiolate anions by nucleophilic substitution between potassium thioacetate and alkyl halides followed by fragmentation. Further reactions of these thiolate anions with substituted (E,Z)-β-styryl halides gave the corresponding sulfides with retention of stereochemistry in good to excellent yields. This procedure does not require a metal catalyst, it proceeds under mild conditions and in short times, and it is free from malodorous and air-sensitive alkyl thiols. Copyright
Stereoconservative formation and reactivity of α-chalcogen- functionalized vinyllithium compounds from α-bromo-vinylic chalcogenides
Braga, Antonio L.,Zeni, Gilson,De Andrade, Leandro H.,Silveira, Claudio C.
, p. 595 - 596 (2007/10/03)
Bromine/lithium exchange was performed upon treatment of α-bromo-vinylic chalcogenides with butyllithium in hexane at room temperature to provide α-chalcogen-vinyllithium intermediates quantitatively. Addition of electrophiles to the lithiated compounds g