Categories: C-C Bond Formation > Chains > Alkynes >
Synthesis of substituted 1,3-diynes
Name Reactions
Recent Literature
A carbenoid Fritsch-Buttenberg-Wiechell (FBW) rearrangement of a substituted
dibromoolefinic precursor is used to generate a lithium acetylide, and
subsequent trapping with carbon-based electrophiles provides a wide range of di-
and triynes. The lithium acetylide formed from the FBW reaction can also undergo
transmetalation to provide zinc, copper, tin, or platinum acetylides.
T. Luu, Y. Morisaki, N. Cunningham, R. R. Tykwinski, J. Org. Chem., 2007,
72, 9622-9629.
A facile and environmentally friendly synthetic method for a variety of
symmetrical 1,3-diyne derivatives is based on a Pd/C-CuI-catalyzed homocoupling
reaction of terminal alkynes. The reaction was efficiently catalyzed by an
extremely low loading of Pd/C and CuI in the presence of molecular oxygen as the
oxidant without any phosphine ligands and bases.
T. Kurita, M. Abe, T. Maegawa, Y. Monguchi, H. Sajiki, Synlett, 2007,
2521-2524.
A palladium-catalyzed dimerization of terminal acetylenes with iodosylbenzene as oxidant allowed the preparation of various diynes in good yields in a short period of time at room temperature.
J. Yan, F. Lin, Z. Yang, Synthesis, 2007, 1301-1303.
