Categories: C-C Bond Formation > Chains >
Synthesis of substituted allenes
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Recent Literature
The palladium-catalyzed of triorganoindium reagents to propargylic esters
afforded via an SN2' rearrangement allenes in good yields and with high
regioselectivity. The reaction of chiral, nonracemic propargylic esters
takes place with high anti-stereoselectivity providing allenes with
high enantiomeric excess.
R. Riveiros, D. Rodríguez, J. P. Sestelo, L. A. Sarandeses, Org. Lett.,
2006,
8, 1403-1406.
1,1-diarylpropadienes and 1,3-diarylpropynes can be prepared by the
sequential lithiation of 1-aryl-1-propynes, transmetalation, and the
corresponding Pd(0)-catalyzed cross-coupling with aryl halides.
S. Ma, Q. He, X. Zhang, J. Org. Chem., 2005,
70, 3336-3338.
Arynes, generated in situ from ortho-silylaryl triflates, undergo ene
reaction with alkynes possessing propargylic hydrogen in the presence of
KF/18-crown-6 in THF at room temperature to give substituted phenylallenes
in good to moderate yields.
T. T. Jayanth, M. Jeganmohan, M.-J. Cheng, S.-Y. Chu, C.-H. Cheng, J. Am.
Chem. Soc.,
2006,
128, 2232-2233.
Various arylallenes and alkenylallenes were prepared via coupling of
allenylstannanes with aryl iodides or alkenyl iodides in the presence of Pd(PPh3)4
as catalyst, LiCl, and DMF as solvent.
C.-W. Huang, M. Shanmugasundaram, H.-M. Chang, C.-H. Cheng,
Tetrahedron, 2003, 59, 3635-3641.
Enantioenriched propargyl mesylates or perfluorobenzoates react with α-(N-carbamoyl)alkylcuprates
to afford scalemic α-(N-carbamoyl) allenes. Subsequent N-Boc
deprotection and AgNO3-promoted cyclization afford enantioenriched
N-alkyl-3-pyrrolines.
R. K. Dieter, N. Chen, V. K. Gore, J. Org. Chem., 2006,
71, 8755-8760.
Homoallenic alcohols are prepared from various propargyl vinyl ethers using a
trinuclear gold(I)-oxo complex, [(Ph3PAu)3O]BF4,
as a catalyst for propargyl Claisen rearrangement at room temperature.
B. D. Sherry, F. D. Toste, J. Am. Chem. Soc.,
2004,
126, 15978-15979.
Various arylallenes and alkenylallenes were prepared via coupling of
allenylstannanes with aryl iodides or alkenyl iodides in the presence of Pd(PPh3)4
as catalyst, LiCl, and DMF as solvent.
C.-W. Huang, M. Shanmugasundaram, H.-M. Chang, C.-H. Cheng, Tetrahedron,
2003, 59, 3635-3641.
