Mitsunobu Reaction The Mitsunobu reaction uses triphenylphosphine (PPh3) and diethyl azodicarboxylate (DEAD) to convert a 1° or 2° alcohol into a wide variety of final products, dependent on the mildly acidic nucleophile (H-Nuc) used. H-Nuc transfers its proton to the zwitterionic adduct formed from PPh3 attacking the DEAD. The resulting...

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Negishi cross coupling The use of organozinc reagents in the Negishi (Pd- or Ni-catalyzed) cross-coupling reaction with organohalides allows for a much greater functional group tolerance than in the Kumada cross-coupling reaction. Other benefits include high reactivity, high regio- and stereoselectivity, few side reactions and little toxicity. Unlike the addition...

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Perkin Reaction Generating α,β-unsaturated carboxylic acids (cinnamic acid derivatives) in the presence of a weak base from aromatic aldehydes with the anhydrides of aliphatic carboxylic acids is known as the Perkin reaction. An enolate intermediate is made from the anhydride, which undergoes a condensation reaction with benzaldehyde, followed by an...

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Popular since the early 1900s, the 1,4-addition of Michael donors to activated π-systems (called Michael acceptors) to form new C-C bonds is known as the Michael addition or reaction. With the help of a base, the donor is converted to an enolate ion, which attacks the Michael acceptor. When a...

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The Mitsunobu reaction uses triphenylphosphine (PPh3) and diethyl azodicarboxylate (DEAD) to convert a 1° or 2° alcohol into a wide variety of final products, dependent on the mildly acidic nucleophile (H-Nuc) used. H-Nuc transfers its proton to the zwitterionic adduct formed from PPh3 attacking the DEAD. The resulting phosphonium intermediate...

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The Mukaiyama aldol reaction uses a catalytic Lewis acid (e.g. TiCl4) or base, and an aqueous work-up to convert an aldehyde and an E- or Z-enol silane to an anti- and/or syn-diastereomer 1,3-ketol. The aldehyde is activated for nucleophilic attack when it coordinates to the Lewis acid, releasing a chloride...

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