Abstract
An efficient direct oxidation method was developed to oxidize some aromatic and aliphatic aldehydes to esters by the dual utilization of NaIO4 and Pd-C. At ambient conditions, various aldehydes were employed in a clean esterification reaction to afford numerous esters in good to excellent yields. By this adopted method, some multifunctional aldehydes, high-energy-containing aromatic and unsaturated aldehydes, were advantageously oxidized to esters without noticeable difficulties. Moreover, no over-oxidation occurred to alcohols, and mostly by products were not formed during this oxidation process. Conventional and some modern methods lag behind owing to their easier operability and easy work-up process. This investigation has proven that the required oxidant (NaIO4) or catalyst (Pd-C) is useless to employ in excess, although some current methods utilize hugely expensive reagents for such conversions. Mundane reaction set-up, easy product recovery technique, nontoxic catalyst, and cheap and available starting materials are the noteworthy advantages of this method.
Graphical Abstract
[http://dx.doi.org/10.1021/op034191c]
[http://dx.doi.org/10.1021/ol400785d] [PMID: 23614873]
[http://dx.doi.org/10.1021/ja104341h]
[http://dx.doi.org/10.1111/cote.12037]
[http://dx.doi.org/10.1021/om800549q]
[http://dx.doi.org/10.1021/ol100302e] [PMID: 20491432]
[http://dx.doi.org/10.1021/ol800176p] [PMID: 18345679]
[http://dx.doi.org/10.1016/j.tifs.2017.09.004]
[http://dx.doi.org/10.1177/9.3.325] [PMID: 14004204]
[http://dx.doi.org/10.13140/RG.2.2.19518.79682]
[http://dx.doi.org/10.1021/ol990383+] [PMID: 10814382]
[http://dx.doi.org/10.1002/ange.19901020837]
[http://dx.doi.org/10.1007/978-3-642-51364-0_52]
[http://dx.doi.org/10.1002/cber.189502803176]
[http://dx.doi.org/10.1021/acs.orglett.5b01579] [PMID: 26161512]
[http://dx.doi.org/10.1002/anie.201008073] [PMID: 21480446]
[http://dx.doi.org/10.1021/jo0606103] [PMID: 16872217]
[http://dx.doi.org/10.1016/j.tetlet.2012.04.111]
[http://dx.doi.org/10.1007/s43630-021-00160-5] [PMID: 35050487]
[http://dx.doi.org/10.1021/acs.orglett.2c02560] [PMID: 36121710]
[http://dx.doi.org/10.1002/ejoc.200801176]
[http://dx.doi.org/10.1021/jo9817164]
[http://dx.doi.org/10.1016/j.tet.2007.10.003]
[http://dx.doi.org/10.1021/ja063476c] [PMID: 17017775]
[http://dx.doi.org/10.1021/acs.joc.3c00729] [PMID: 37307498]
[http://dx.doi.org/10.1246/cl.1978.17]
[http://dx.doi.org/10.1016/S0040-4039(01)90372-7]
[http://dx.doi.org/10.1016/j.jscs.2015.12.007]
[http://dx.doi.org/10.1002/jccs.201600777]
[http://dx.doi.org/10.1021/ol052120n] [PMID: 16235964]