Categories: C-C Bond Formation > Arenes >
Propargylic Substitution, Propargylation
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Recent Literature
A catalytic asymmetric Negishi cross-coupling of racemic secondary propargylic
halides with arylzinc reagents has been developed using commerically available
catalyst components (NiCl2·glyme and pybox as ligand).
S. W. Smith, G. C. Fu, J. Am. Chem. Soc., 2008,
130, 12645-12647.
PMA-silica gel catalyzes efficiently the propargylation of aromatic compounds
with arylpropargyl alcohols in the absence of solvent under environmentally
benign conditions.
P. Srihari, J. S. S. Reddy, S. S. Mandal, K. Satyanarayana, J. S. Yadav, Synthesis, 2008,
1853-1860.
p-Toluenesulfonic acid efficiently catalyzes direct nucleophilic
substitutions of the hydroxy groups of propargylic alcohols with a large
variety of carbon- and heteroatom-centered nucleophiles. Reactions can be
conducted under mild conditions and in air without the need for dried
solvents.
R. Sanz, A. Martinez, J. M. Alvarez-Gutierrez, F. Rodriquez, Eur. J. Org.
Chem., 2006, 1383-1386.
A general and efficient FeCl3-catalyzed substitution reaction of
propargylic alcohols with carbon- and heteroatom-centered nucleophiles such
as allyl trimethylsilane, alcohols, aromatic compounds, thiols, and amides,
forms new C-C, C-O, C-S and C-N bonds.
Z.-P. Zhan, J.-L. Yu, Y.-Y. Cui, R.-F. Yang, W.-Z. Yang, J.-P. Li, J. Org. Chem., 2006,
71, 8298-8301.
