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Synthesis of substituted allenes

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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.