The Sakurai reaction (also known as the Hosomi–Sakurai reaction) is the chemical reaction of carbon electrophiles (such as a ketone shown here) with allyltrimethylsilane catalyzed by strong Lewis acids.[1][2][3] The reaction achieves results similar to the addition of an allyl Grignard reagent to the carbonyl.
The Sakurai reaction
Strong Lewis acids such as titanium tetrachloride, boron trifluoride, tin tetrachloride, and AlCl(Et)2 are all effective in promoting the Hosomi reaction. The reaction involves electrophilic allyl shift via a beta-silyl carbocationic intermediate, the beta-silicon effect.[4]
^Hosomi, Akira (1 May 1988). "Characteristics in the reactions of allylsilanes and their applications to versatile synthetic equivalents". Accounts of Chemical Research. 21 (5): 200–206. doi:10.1021/ar00149a004. ISSN 0001-4842.
^Fleming, Ian; Dunoguès, Jacques; Smithers, Roger (2004), "The Electrophilic Substitution of Allylsilanes and Vinylsilanes", Organic Reactions, American Chemical Society, pp. 57–575, doi:10.1002/0471264180.or037.02, ISBN 9780471264187
^Fleming, Ian (1 January 1991). "Allylsilanes, Allylstannanes and Related Systems". In Trost, Barry M.; Fleming, Ian (eds.). 2.2 – Allylsilanes, Allylstannanes and Related Systems. Pergamon. pp. 563–593. doi:10.1016/b978-0-08-052349-1.00041-x. ISBN 9780080523491. {{cite book}}: |work= ignored (help)
^"Hosomi-Sakurai Reaction". organic-chemistry.org. Retrieved 1 September 2019.
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