Iron(0)-Mediated Henry-Type Reaction of Bromonitromethane with Aldehydes for the Efficient Synthesis of 2-Nitro-alkan-1-ols

Abstract

The Henry-type reaction of bromonitromethane with various aldehydes for the efficient synthesis of 2-nitro-alkan-1-ols by using inexpensive and commercial iron powder as reaction mediator was developed. The reaction proceeded efficiently in the presence of PbCl2 and tetrabutylammonium hydrogen sulfate (TBAHS) to produce the desired products in moderate to good yield with wide functional group tolerance.

Iron-Mediated Reductive Amidation of Triazine Esters with Nitroarenes

“…Although different carbonyl derivatives (e.g., ester, amide) have been employed to couple with nitroarenes for amide syntheses, − the use of triazine ester as acylation reagent to react with nitroarene under reductive conditions for accessing amide has not been developed thus far. In addition, in contrast to iron metal which is undoubtedly the most widely abundant and the cheapest metal on earth, , the previously developed methods required the use of relatively expensive and more reactive metals (e.g., Mg, Zn, Mn) in the presence or absence of transition metal catalyst (e.g., Ni, Cr). − In continuation of our endeavors in developing iron(0)-mediated organic transformations and reductive cross-coupling reactions, Herein, we report an iron-mediated reductive amidation of triazine esters with nitroarenes in the presence of TMSCl in DMF, providing facile entry to amides in moderate to good yields with good functionality compatibility (Scheme b).…”