Final published version
Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
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TY - JOUR
T1 - 1,4-Butanediol as a Reducing Agent in Transfer Hydrogenation Reactions
AU - Maytum, Hannah
AU - Francos, Javier
AU - Whatrup, David J.
AU - Williams, Jonathan M. J.
PY - 2010
Y1 - 2010
N2 - 1,4-Butanediol is able to deliver two equivalents of H(2) in hydrogen-transfer reactions to ketones, imines, and alkenes. Unlike simple alcohols, which establish equilibrium in the reduction of ketones, 1,4-butanediol acts essentially irreversibly owing to the formation of butyrolactone, which acts as a thermodynamic sink. It is therefore not necessary to use 1,4-butanediol in great excess in order to achieve reduction reactions. In addition, allylic alcohols are reduced to saturated alcohols through an isomerization/reduction sequence using a ruthenium catalyst with 1,4-butanediol as the reducing agent. Imines and alkenes are also reduced under similar conditions.
AB - 1,4-Butanediol is able to deliver two equivalents of H(2) in hydrogen-transfer reactions to ketones, imines, and alkenes. Unlike simple alcohols, which establish equilibrium in the reduction of ketones, 1,4-butanediol acts essentially irreversibly owing to the formation of butyrolactone, which acts as a thermodynamic sink. It is therefore not necessary to use 1,4-butanediol in great excess in order to achieve reduction reactions. In addition, allylic alcohols are reduced to saturated alcohols through an isomerization/reduction sequence using a ruthenium catalyst with 1,4-butanediol as the reducing agent. Imines and alkenes are also reduced under similar conditions.
KW - hydrogenation
KW - isomerization
KW - lactones
KW - reduction
KW - ruthenium
KW - ASYMMETRIC TRANSFER HYDROGENATION
KW - DEHYDROGENATIVE CYCLIZATION
KW - RENEWABLE RESOURCES
KW - BORROWING HYDROGEN
KW - SUCCINIC ACID
KW - ALCOHOLS
KW - LACTONES
KW - ALDEHYDES
KW - DIOLS
KW - 1,4-ALKYNEDIOLS
U2 - 10.1002/asia.200900527
DO - 10.1002/asia.200900527
M3 - Journal article
VL - 5
SP - 538
EP - 542
JO - Chemistry - An Asian Journal
JF - Chemistry - An Asian Journal
SN - 1861-4728
IS - 3
ER -