Does anyone know when we use heck reaction or suzuki reaction? I came across some example...

Does anyone know when we use heck reaction or suzuki reaction? I came across some example but not sure when to use each reaction? I thought they are the same?

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Expert Solution

Both reactions are metal-catalyzed cross-coupling reactions. But they are not the same.

(1) The reaction mechanisms of both reactions are different. I have given mechanisms of both reactions in the following figure. Heck reaction involves with oxidative addition,Syn-migratory Insertion Syn-beta- hydride Elimination.

Suzuki reaction involves with Oxidative addition, Transmetalation, Reductive Elimination

(2) Base is required in Heck reaction to regenerate Pd(II) to Pd(0). Base is not required in Suzuki reaction.

Suzuki reaction: The coupling reaction between aryl halides and activated alkenes in the presence of Pd catalyst.

Heck reaction: The coupling reaction between aryl halides and activated boronic acid in the presence of Pd catalyst.

The main difference is the second coupling partner

In Suzuki, second coupling partner is Boronic acid

In Heck second coupling partner is alkenes

Heck reaction is useful for alkenylation (olefination) to connect alkene with aryl moieties. Generally, Suzuki reaction is useful for arylation to connect two aryl moieties (but not limited for only aryl moieties).

queen_honey_blossom answered 9 months ago

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