Gold-Catalyzed Intermolecular

CS Bond Formation: Efficient

Synthesis of -Substituted
Vinyl Sulfones
Literature Report
Violet Chen

Background
covalent protease inhibitors
good Michael acceptors
trap nucleophiles by forming stable covalent
adducts
best if the -C is less hindered than the -C





-vinyl sulfones
substrates for bio-conjugation


Current Methods
elimination from - or -substituted
sulfones
oxidation of vinyl sulfides
olefination reactions (Wittig, Horner-
Wadsworth-Emmons,Julia)


Current Methods (contd)
Drawbacks
toxic Hg, Se-containing starting materials
poor atom economy
only give trans -substituted products
=> preference for anti-Markovnikov
addition
limited substrate scope
poor / regioselectivity


This Reaction
Reaction Optimization
BrettPhos
XPhos
IPr
Alkyne Substrate Scope
Sulfinic Acid Substrate Scope
Examples
good endo-selectivity
-substituted vinyl
sulfones are much
better Michael
receptors than -
substituted vinyl
sulfones
Conclusion
A general, regioselective, and efficient
method for the synthesis of -
substituted vinyl sulfones from terminal
alkynes and sulfinic acids using an Au(I)
catalyst and a Ga(III) Lewis acid
Important applications in the biological
and pharmaceutical sciences

Thank you for your attention !