Liebeskind–Srogl coupling

[1] This reaction was invented by and named after Jiri Srogl from the Academy of Sciences, Czech Republic, and Lanny S. Liebeskind from Emory University, Atlanta, Georgia, USA.

The original transformation used catalytic Pd(0), TFP = tris(2-furyl)phosphine as an additional ligand and stoichiometric CuTC = copper(I) thiophene-2-carboxylate as a co-metal catalyst.

Liebeskind-Srogl reaction is most commonly seen with sulfide or thioester electrophiles and boronic acid or stannane nucleophiles but many other coupling partners are viable.

[1] Second generation approach renders the reactions catalytic in copper by using an extra equivalent of boronic acid under aerobic, palladium free conditions.

Metal templating by Cu(II/III) acts as a Lewis acid to both activate the thiol ester and deliver R2 (from either boron directly or via an intermediate Cu-R2 species), which produces the ketone and a Cu-thiolate.

[12] The Guerrero lab used the Liebeskind–Srogl coupling to construct the entire carbon skeleton of viridin in high yield on multi-gram scale.

[13] The lab of Figadere used the Liebeskind–Srogl coupling early in their synthesis of amphidinolide F[14] by employing this reaction to construct the north eastern fragment of the macrocycle and the terpene chain.