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Keck Radical Allylation

Keck radical allylation   Named Reactions in Organic Synthesis

Reaction category:
Radical reactions!

Other featured reactions:

 

First reported separately by Masanori Kosugi and Jean Grignon in 1973, the coupling of an alkyl halide with allyltributyltin under radical conditions to insert an allyl group was employed in the total synthesis of perhydrohistrionicotoxin by Gary Keck and colleagues. After he had determined the scope of this reaction it became known as the Keck radical allylation. To initiate the process, AIBN (azobisisobutyronitrile) was found to be the most efficient catalyst and the reaction was found to be general for primary, secondary and tertiary alkyl bromides. The reaction is highly chemoselective, tolerates a wide range of functional groups and is tolerant of steric hindrance.

This reaction has been utilized successfully in a number of total synthesis campaigns, including that of the Stemona alkaloid (-)-tuberostemonine by Peter Wipf and the anti-cancer alkaloid manzamine A by David J. Hart.

Mechanism of the Keck radical allylation reaction

Reaction mechanism of the Keck radical allylation


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Other reaction categories:

Electrophilic aromatic substitution

Nucleophilic substitution reactions

Heterocycle-formation

Transition metal-catalyzed couplings

Oxidation

Reactions involving carbonyl compounds

Reduction reactions

Rearrangement reactions

Electrophilic addition reactions


Relevant Alfa Aesar product for the Keck radical allylation:

Allyltri-n-butyltin, 97%

We have many alkyl halides in our portfolio.

 

 

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