Categories: C-C Bond Formation > Arenes >
Propargylic Substitution, Propargylation
| Related: |
 |
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.
A copper-catalyzed substitution reaction of propargylic ammonium salts with aryl
Grignard reagents is stereospecific and α-regioselective and proceeds with
exceptional functional group tolerance.
M. Guisán-Ceinos, V. Martín-Heras, M. Tortosa, J. Am. Chem. Soc., 2017,
139, 8448-8451.
A chiral sulfinamide phosphine ligand enables a Pd-catalyzed enantioselective
three-component coupling of N-tosylhydrazones, aryl halides, and terminal
alkynes under mild conditions utilizing (GF-Phos) to provide chiral
diarylmethyl alkynes. This reaction features readily available starting
materials, general substrate scope, high enantioselectivity, and ease of
scale-up.
G. Zhao, Y. Wu, H.-H. Wu, J. Yang, J. Zhang, J. Am. Chem. Soc.,
2021, 143, 17983-17988.
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.