Exploration of tin-catalyzed phosphine dehydrocoupling: Catalyst effects and observation of tin-catalyzed hydrophosphination

The phosphine substrate scope in dehydrocoupling reactions catalyzed by Cp-2*SnCl2 (Cp* = pentamethylcyclopentadienyl, 1) have been explored. Catalyst variants R2SnX2 (R = Cp*, Ph; X = Cl, Me, Ph) were also tested, which revealed that activity is dependent on the Cp* ligands as well as more electron withdrawing X ligands. Steric factors at the phosphine substrate are also important. Compound 1 was found to be a catalyst for hydrophosphination of styrene, 2,3-dimethylbutadiene, and diphenylacetylene with phenylphosphine, which is the first example of a p-block catalyst for hydrophosphination. (C) 2014 Elsevier B. V. All rights reserved.