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Synthesis of alkylstannanes

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A transition metal free stannylation reaction of alkyl bromides and iodides with hexamethyldistannane is operationally convenient and fast and offers good functional group tolerance. A wide range of functionalized primary and secondary alkyl and benzyl trimethyl stannanes are prepared in good yields.
S. Li, C. Lian, G. Yue, J. Zhang, D. Qiu, F. Mo, J. Org. Chem., 2022, 87, 4291-4297.


Highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannations of cyclopropenes gave multisubstituted cyclopropylstannanes. The addition across the double bond proceeds from the least hindered face.
M. Rubina, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc., 2002, 124, 11566-11567.


A catalytic enantioselective hydrostannation of cyclopropenes allows for the efficient synthesis of 2,2-disubstituted cyclopropylstannanes with high degrees of diastereo- and enantioselectivity. The facial selectivity of this reaction is entirely controlled by steric factors.
M. Rubina, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc., 2004, 126, 3688-3689.


Highly efficient, stereo- and regioselective palladium-catalyzed hydro-, sila-, and stannastannations of cyclopropenes gave multisubstituted cyclopropylstannanes. The addition across the double bond proceeds from the least hindered face.
M. Rubina, M. Rubin, V. Gevorgyan, J. Am. Chem. Soc., 2002, 124, 11566-11567.


A new method for the synthesis of substituted 2-acylallylmetal reagents in a highly regio- and stereoselective fashion involving a three-component assembly of allenes, acyl chlorides, and bimetallic reagents (B-B, Si-Si, and Sn-Sn) catalyzed by phosphine-free palladium complexes is described.
F.-Y. Yang, M. Shanmugasundaram, S.-Y. Chuang, P.-J. Ku, M.-Y. Wu, C.-H. Cheng, J. Am. Chem. Soc., 2003, 125, 12576-12583.