Categories: C-Sn Bond Formation >
Synthesis of alkylstannanes
Recent Literature
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.