Metal-free, room temperature, acid-K₂S₂O₈ mediated method for the nitration of olefins: an easy approach for the synthesis of nitroolefins

Abstract

Here, we have developed a simple, room temperature method for the nitration of olefins by using inexpensive sodium nitrite as a source of nitro groups in the presence of TFA and potassium persulphate under an open atmosphere.

Reducing-Agent-Free Convergent Synthesis of Hydroxyimino-Decorated Tetracyclic Fused Cinnolines via RhIII-Catalyzed Annulation Using Nitroolefins

“…Nitroolefins were prepared according to the literature reported procedure and identified by comparison of melting point/ 1 H NMR with the literature melting point/ 1 H NMR: 3a – c , 3d , 3e , 3f – i , 3j , 3l , 3m , and 3n – q and completely characterized with the detailed spectroscopic studies.…”

Metal‐free Synthesis of β‐Nitrostyrenes via DDQ‐Catalyzed Nitration

“…Singh et al . published another simple stereoselective formation of nitrostyrenes using sodium nitrite and K 2 S 2 O 8 in the presence of trifluoroacetic acid as well 8 . All of these reactions granted an easy preparation of β‐nitrostyrenes, but it is necessary to execute the reactions at high temperature or use stoichiometric amounts of oxidants or strong acid.…”

“…Most recently, several research groups overcome such problems by using appropriate combination of nitrogen sources and mild oxidants under transition-metal free conditions (Scheme 1). [6][7][8] Maiti et al developed the practical stereoselective nitration of styrenes with tert-butyl nitrite (TBN) and 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO). 6 Guo group also reported the nitration reactions of olefins with sodium nitrite, K 2 S 2 O 8 using TEMPO.…”

Recent Advances in the Nitration of Olefins

“…In the last decades several research groups devised new methods for the direct nitration of olefins which are shown in scheme 21. [51][52][53][54] Katayev and co-workers in 2019 designed and developed a practical and bench-stable succinimide derived NO 2 -transfer reagent can liberate nitryl radical under mild and neutral conditions, thus allowing for the direct nitration of C(sp 2 )À H bonds of alkenes (Scheme 22). [55] This protocol also allows to access valuable nitrohydrin building blocks and functionalised isoxazole-motifs in an unprecedented and selective fashion using a single reagent in one-step.…”

“…While our original reports were published in the year 2013, several notable development in the related field appeared in the literature in the subsequent years. In the last decades several research groups devised new methods for the direct nitration of olefins which are shown in scheme 21 [51–54] …”