Iron nitrate/TEMPO-catalyzed oxidative Passerini reaction of alcohols in air

Abstract

The oxidative three-component Passerini reaction using primary alcohols as aldehyde surrogates with ferric nitrate (Fe(NO 3 ) 3 .9H 2 O) and TEMPO as the catalyst system under air is described, The reaction has broad scope over all three components.

Synthesis of (1,4-benzoxazinones-3-yl)malonate derivatives via cross-dehydrogenative-coupling reactions under ball-milling conditions

“…[17][18][19][20] Iron is one of the most abundant elements on Earth and iron salts act as catalyst for several chemical transformations, 21 while they are inexpensive and nonharmful to humans and the environment. 22,23 These features make various types of iron catalysts very popular in organic synthesis and have resulted in many applications in recent decades. In continuation of our investigations in heterocyclic chemistry, 25,26 we recently reported a ballmilled/Fe(II)-catalyzed CDC of 1,4-benzoxazinones with indoles.…”

Electromediated Alcohol-Based Passerini-Type Reaction

“…23 pioneered this field and reported a multicatalytic system based on a copper (II) salt, TEMPO, and sodium nitrite, which operates under oxygen atmosphere (Scheme 1, (b)). Since then, a very similar iron-catalyzed process was reported by Batra et coll., 24 and Karimi and Farhangi developed a magnetically recyclable TEMPO derivative acting as an heterogenous catalyst. 25 Based on our expertise in electro-oxidative IMCRs, we decided to study the feasibility of a metal-and oxygen-free electrochemical alternative to such alcohol-based Passerini type coupling (Scheme 1, (c)).…”