An enantioselective hydrogenation of disubstituted furans has been developed by using a chiral ruthenium catalyst with N-heterocyclic carbene ligands. This reaction converts furans into valuable enantioenriched disubstituted tetrahydrofurans.

The Pd-catalyzed reaction of N-tosylhydrazones and arylboronic acids provides olefin derivatives. This oxidative cross-coupling is suggested to proceed through a migratory insertion process of a Pd carbene intermediate.

Here we report the facile formation of boron-containing cyclic (amino)(imino)carbene complexes by reaction of a chromium borylene complex [(OC)(5)Cr=B=N(SiMe(3))(2)] with isocyanides.

Propargylic sulfides and dithioacetals are found to undergo similar transformations as propargylic carboxylates when catalyzed by AuCl or AuCl3, affording indene derivatives through pentannulation of aromatic rings. The reaction presumably involves Au carbene as the reactive intermediate.

An efficient N-heterocyclic carbene (NHC) catalyzed sulfenylation reaction of α,β-unsaturated aldehydes with N-(arylthio)phthalimide has been developed. A wide variety of α-thioenals can be obtained with good to excellent yields and excellent Z-configuration.

The use of in situ generated (NHC)-Ni catalytic species (NHC = N-heterocyclic carbene) allows for the synthesis, in short reaction times, of a variety of tertiary alcohols from secondary alcohols through a domino oxidation-addition protocol.

Enantioselective modification of sulfonamides and sulfonamide-containing drugs via carbene organic catalysis is disclosed. The cation?? interaction was computationally found to play a pivotal role in modulating the reaction enantioselectivity.

Thiazolium carbene-catalyzed reaction of aromatic 1,2-diketones with enones in aprotic solvents gave double acylation products in good yields, whereas hydroacylation products formed by Stetter reaction were not detected at all. These results suggested the generation of aroyloxyenamine species from the 1,2-diketones instead of hydroxyenamines (Breslow intermediates).

An N-heterocyclic carbene-catalyzed β-hydroxylation of enals is developed. The reaction goes through a pathway involving multiple radical intermediates, as supported by experimental observations. This oxidative single-electron-transfer reaction allows for highly enantioselective access to β-hydroxyl esters that are widely found in natural products and bioactive molecules.

The gold(I)-catalyzed reaction of water with o-acetylenyl-substituted phenyldiazoacetates provides 1H-isochromene derivatives in good yields. The reaction follows a catalytic sequence of gold carbene formation/water O-H insertion/alcohol-alkyne cyclization. The gold(I) complex is the only catalyst in each of these steps.