Mitsunobu Reaction
10.4 هزار بار بازدید -
4 سال پیش
-
The Mitsunobu Reaction allows the
The Mitsunobu Reaction allows the conversion of primary and secondary alcohols into different functional groups using triphenylphosphine and an azodicarboxylate. The reaction proceeds with inversion of configuration (SN2).
General features:
1. It is best suited for primary and secondary alcohols. Generally, tertiary alcohols don't react.
2. Carboxylic acids afford esters; alcohols and phenols, ethers; thiols, thioethers.
3. The reaction is usually conducted in THF. Dioxane and DCM are also suitable.
4. PPh3 are the most common phosphines used.
5. DEAD and DIAD are the most common azodicarboxylate reagents used.
Reaction mechanism:
1. Triphenylphosphine reacts with DEAD producing a betaine intermediate that deprotonates the nucleophile.
2. Formation of the oxyphosphonium ion.
3. Nucleophilic attack of the nucleophile in an SN2 fashion generates the final product.
Pinterest:
https://www.pinterest.es/pin/67166973...
References:
NROChemistry: https://nrochemistry.com/mitsunobu-re...
Seminal publication:
Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382. https://www.journal.csj.jp/doi/pdf/10...
General features:
1. It is best suited for primary and secondary alcohols. Generally, tertiary alcohols don't react.
2. Carboxylic acids afford esters; alcohols and phenols, ethers; thiols, thioethers.
3. The reaction is usually conducted in THF. Dioxane and DCM are also suitable.
4. PPh3 are the most common phosphines used.
5. DEAD and DIAD are the most common azodicarboxylate reagents used.
Reaction mechanism:
1. Triphenylphosphine reacts with DEAD producing a betaine intermediate that deprotonates the nucleophile.
2. Formation of the oxyphosphonium ion.
3. Nucleophilic attack of the nucleophile in an SN2 fashion generates the final product.
Pinterest:
https://www.pinterest.es/pin/67166973...
References:
NROChemistry: https://nrochemistry.com/mitsunobu-re...
Seminal publication:
Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382. https://www.journal.csj.jp/doi/pdf/10...
4 سال پیش
در تاریخ 1399/06/15 منتشر شده
است.
10,451
بـار بازدید شده