Table 1.

Ruthenium(0) catalyzed hydrohydroxyalkylation of 1-phenyl-1-propyne 2a with diols 1a-1l.^a

^aYields are of material isolated by silica gel chromatography. C₁₀H₁₅CO₂H refers to 1-adamantanecarboxylic acid. For acyclic 1,2-diols, the terminology “cis” and “trans” relates to the indicated reactant conformation. See Supporting Information for further details.

^bThe cis-1,2-diol was employed.

^cThe trans-1,2-diol was employed.

^d2 h.

^eA mixture of cis- and trans-1,2-diols was employed

^fDPPF (6 mol%) was used instead PCy₃ (12 mol%).

^g20 h.