Transition Metal Free Stannylation of Alkyl Halides: The Rapid Synthesis of Alkyltrimethylstannanes
Songyi Li, Chang Lian, Guanglu Yue, Jianning Zhang, Di Qiu* and Fanyang Mo*
*Tianjin Normal University, Tianjin 300387; Peking University, Beijing 100871, China, Email:
hxxyqiudi
mail.tjnu.edu.cn, fmopku.edu.cn
S. Li, C. Lian, G. Yue, J. Zhang, D. Qiu, F. Mo, J. Org. Chem., 2022, 87, 4291-4297.
DOI: 10.1021/acs.joc.1c03135
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Abstract
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.
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Procedure for stannylation of alkyl bromides
t-BuOLi (0.45 mmol, 1.5 equiv., 36 mg) was weighted in a 10 mL reaction tube under nitrogen atmosphere. DMF (2.0 mL), hexamethyldistannane (0.36 mmol, 1.2 equiv., 118 mg, 75 μL) and bromide (0.3 mmol, 1.0 equiv.) were then sequentially added. The reaction solution was stirred in an oil bath for 1 h at 80 °C. Then the reaction system was filtered by flash column chromatography to remove the insoluble precipitate, and then the crude product was purified by silica gel column chromatography to obtain the desired alkyltrimethylstannane.
Key Words
ID: J42-Y2022
