CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions
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CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions. / Juhl, Martin; Petersen, Allan R.; Lee, Ji-Woong.
In: Chemistry: A European Journal, Vol. 27, No. 1, 2021, p. 228-232.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - CO2-Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions
AU - Juhl, Martin
AU - Petersen, Allan R.
AU - Lee, Ji-Woong
N1 - A previous version of this manuscript has been deposited on a preprint server (https://doi.org/10.26434/chemrxiv.12652361.v1).
PY - 2021
Y1 - 2021
N2 - Abstract Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani?Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.
AB - Abstract Thermodynamic and kinetic control of a chemical process is the key to access desired products and states. Changes are made when a desired product is not accessible; one may manipulate the reaction with additional reagents, catalysts and/or protecting groups. Here we report the use of carbon dioxide to accelerate cyanohydrin synthesis under neutral conditions with an insoluble cyanide source (KCN) without generating toxic HCN. Under inert atmosphere, the reaction is essentially not operative due to the unfavored equilibrium. The utility of CO2-mediated selective cyanohydrin synthesis was further showcased by broadening Kiliani?Fischer synthesis under neutral conditions. This protocol offers an easy access to a variety of polyols, cyanohydrins, linear alkylnitriles, by simply starting from alkyl- and arylaldehydes, KCN and an atmospheric pressure of CO2.
KW - carbon dioxide
KW - cyanohydrins
KW - elongation
KW - homologation
KW - xanthate
U2 - 10.1002/chem.202003623
DO - 10.1002/chem.202003623
M3 - Journal article
C2 - 32812672
VL - 27
SP - 228
EP - 232
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 1
ER -
ID: 261045071