Technical Notes:

1. Precursor to the nucleophilic carbene that serves as a bulky, electron-rich "phosphine mimic" for metal-catalyzed reactions .

(a) Palladium-catalyzed Suzuki cross-coupling of aryl chlorides .

(b) Palladium-catalyzed Kumada cross-coupling of aryl chlorides.

(c) Ruthenium-carbene catalysts for ring-closing metathesis.

(d) Suzuki coupling of aryltrimethylammonium salts .

(e) Sonogashira coupling of aryl bromides .

2.Precursor to a nucleophilic carbene that serves as catalyst.

3.L igand for arylation of aldehydes .

4.L igand for carbene catalyzed inte rmolecular arylation of C-H bonds.

5.Catalyst for boron conjugate additions to cyclic and acyclic a,ß-unsaturated carbonyls.

6.Ligand for dehydrogenative cyclocondensation of aldehydes, alkynes, and dialkylsilanes.

7.Precursor for carbene for conjugate silylation of alpha, beta-unsaturated carbonyls.