Rhodium-catalyzed oxygenative addition to terminal alkynes for the synthesis of esters, amides, and carboxylic acids.
A gem of a couple: The title reaction of terminal alkynes with O and N nucleophiles proceeds in the presence of [{Rh(cod)Cl}2], P(4-FC6H4)3, and 4-picoline N-oxide. Alcohols, amines, and water add to the terminal alkynes to give esters, amides, and carboxylic acids, respectively. The reaction involves formation of a rhodium vinylidene, oxidation to a ketene by oxygen transfer, and nucleophilic addition.
Department of Chemistry, Seoul National University, Seoul 151-747 (Republic of Korea) http://cbleegroup.snu.ac.kr/
Insu
I
Kim
Chulbom
C
Lee
alkynes; homogeneous catalysis; oxygenation; rhodium; vinylidene ligands