Categories: C-C Bond Formation > Chains >
Propargylic Substitution
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Recent Literature
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.
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.
The reaction of alkoxides with boron trichloride results in the generation
of cations that can be allylated in subsequent transformations. The absence
of Brønsted acids can make a significant difference in such syntheses.
G. W. Kabalka, M.-L. Yao, S. Borella, J. Am. Chem. Soc., 2006,
128, 11320-11321.
Under different conditions, the reaction of propargyl alcohols and terminal
alkynes leads to the selective formation of 1,4-diynes and polysubstituted
furans/pyrroles. Water is the only byproduct in the atom economic, selective
synthesis of 1,4-diynes and pyrroles, whereas the synthesis of furans is fully
atom economic.
T. Wang, X.-l. Chen, L. Chen, Z.-p. Zhan, Org. Lett., 2011,
13, 3324-3327.
C-O bond cleavage of lithium alkoxides occurs readily at room temperature in the
presence of titanium(IV) halides. Capture of the resultant carbocation by
alkynes provides an efficient route to trisubstituted (E)-alkenyl halides
with high stereoselectivity.
M.-L. Yao, T. R. Quick, Z. Wu, M. P. Quinn, G. W. Kabalka, Org. Lett., 2009,
11, 2647-2649.
Highly substituted α,α-disubstituted β-alkynyl esters are readily prepared from
allenyl esters and either alkyl halide, acid chloride, or alkyl chloroformate,
mediated by an amide base. This highly efficient and mild process tolerates
various functional groups and provides α,α-disubstituted β-alkynyl esters in
good to excellent yields.
W. Wang, B. Xu, G. B. Hammond, Org. Lett.,
2008,
10, 3713-3716.
A one-pot procedure for the synthesis of 2-alkyl-2-arylcyanoacetates based on a
Pd(OAc)2/dppf-catalyzed enolate arylation followed by in situ
alkylation tolerates a diverse range of aryl and heteroaryl bromides, and
provides a rapid entry to a wide range of products in very good to yield.
X. Wang, A. Guram, E. Bunel, G.-Q. Cao, J. R. Allen, M. M. Faul, J. Org. Chem., 2008,
73, 1643-1645.
