Cross-coupling tricyclohexylphosphine

Ishiyama, T., Ishida, K., Miyaura, N. Synthesis of pinacol arylboronates via cross-coupling reaction of bis(pinacolato)diboron with chloroarenes catalyzed by palladium(0)-tricyclohexylphosphine complexes. Tetrahedron 2001, 57, 9813-9816. 

Nickel(O) complexes tend to undergo oxidative addition of aryl halides faster than palladium(O) complexes. There are some drawbacks to the use of the nickel complexes, described above, that can outweigh the lower cost of nickel. Nevertheless, the ruckel complexes containing triarylphosphines do undergo oxidative addition of aryl chlorides (Equation 19.39) and tosylates (Equation 19.40), and some mild conditions have been developed for nickel-catalyzed cross couplings of aryl chlorides and aryl tosylates with ligands such as triphenylphosphine or tricyclohexylphosphine. ... 

A well-known, cross-coupling palladium catalyst [Pd2(dba)3(CHCl3)] in combination with tricyclohexylphosphine has also been found as a good catalyst for regioselective hydrosilylation of functionalized alkynes to yield substituted (E)-alkenylsilanes (62)... 

Trisoxazoles can be accessed from 1,4-dihaloxazoles via a re-gioselective Suzuki-Miyaura cross-coupling, followed by a Stille coupling. Tricyclohexylphosphine functioned as a suitable ligand in both Suzuki and Stille reactions, furnishing the desired products under microwave conditions (eqs 24 and 25). 

---