Oxidative Amidation of Nitroalkanes with Amine Nucleophiles using Molecular Oxygen and Iodine

Angewandte Chemie
Jing LiYujiro Hayashi

Abstract

The formation of amides and peptides often necessitates powerful yet mild reagent systems. The reagents used, however, are often expensive and highly elaborate. New atom-economical and practical methods that achieve such goals are highly desirable. Ideally, the methods should start with substrates that are readily available in both chiral and non-chiral forms and utilize cheap reagents that are compatible with a wide variety of functional groups, steric encumberance, and epimerizable stereocenters. A direct oxidative method was developed to form amide and peptide bonds between amines and primary nitroalkanes simply by using I2 and K2 CO3 under O2 . Contrary to expectations, a 1:1 halogen-bonded complex forms between the iodonium source and the amine, which reacts with nitronates to form α-iodo nitroalkanes as precursors to the amides.

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Citations

Sep 28, 2016·Chemical Reviews·Renata Marcia de FigueiredoJean-Marc Campagne
Sep 30, 2016·Journal of the American Chemical Society·Long HuJunfeng Zhao
May 24, 2017·Organic Letters·Amber A S Gietter-BurchDonald A Watson
May 17, 2017·Chemical Science·Kazuyuki Tokumaru, Jeffrey N Johnston
Oct 28, 2015·Chemical Communications : Chem Comm·Kenneth E Schwieter, Jeffrey N Johnston
Jun 28, 2018·Organic & Biomolecular Chemistry·Abdul MotalebPradip Maity
May 19, 2018·Nature Communications·Pan LiFuwei Li
Oct 14, 2016·Chemistry : a European Journal·Kilian MuñizAlessandro Piccinelli
Feb 23, 2021·Accounts of Chemical Research·Yujiro Hayashi
May 9, 2019·Chem·Michael S CrockerJeffrey N Johnston
Apr 30, 2021·Chemical Communications : Chem Comm·Xiaoling WangYujiro Hayashi

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