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CO 2 ‐Enabled Cyanohydrin Synthesis and Facile Iterative Homologation Reactions **
Author(s) -
Juhl Martin,
Petersen Allan R.,
Lee JiWoong
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202003623
Subject(s) - cyanohydrin , reagent , chemistry , inert gas , cyanide , catalysis , combinatorial chemistry , inert , organic chemistry
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 CO 2 ‐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 CO 2 .