Sakurai reaction

<p>The Sakurai reaction (also known as the Hosomi–Sakurai reaction) is the <a href="/facts/Chemical_reaction/GpqWlKrz">chemical reaction</a> of <a href="/facts/Carbon/ukrgQexo">carbon</a> <a href="/facts/Electrophile/1AHFg1zm">electrophiles</a> (such as a <a href="/facts/Ketone/BqQXpLo4">ketone</a> shown here) with <a href="/facts/Allyltrimethylsilane/mbqc6ssz">allyltrimethylsilane</a> catalyzed by strong <a href="/facts/Lewis_acid/qlLqRvg2">Lewis acids</a>. The reaction achieves results similar to the addition of an allyl <a href="/facts/Grignard_reagent/0vkLtPo1">Grignard reagent</a> to the carbonyl.
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<p>Strong Lewis acids such as <a href="/facts/Titanium_tetrachloride/bGS32SsD">titanium tetrachloride</a>, <a href="/facts/Boron_trifluoride/2qa0NIH8">boron trifluoride</a>, <a href="/facts/Tin_tetrachloride/MgGG3FJJ">tin tetrachloride</a>, and AlCl(Et)2 are all effective in promoting the Sakurai reaction. The reaction involves <a href="/facts/Electrophilic_allyl_shift/T9xfF9rV">electrophilic allyl shift</a> via a beta-silyl carbocationic intermediate, the <a href="/facts/Beta-silicon_effect/EaPmn2Uq">beta-silicon effect</a>.
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Sakurai reaction open-in-new

Sakurai reaction