METAL-FREE FUNCTIONALIZATION OF AZINE <i>N</i>-OXIDES WITH ELECTROPHILIC REAGENTS

Authors

  • Сергей В. Байков Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034
  • Вадим П. Боярский Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

DOI:

https://doi.org/10.1007/5666

Keywords:

azine N-oxides, electrophilic reagents, catalysis by Brønsted acids, C–H functionalization

Abstract

The review is devoted to the reactions of azine N-oxides with electrophilic reagents, which make it possible to functionalize the azine fragment with the formation of a new C–X bond (X = C, N, O, Hal, S, P) without the participation of transition metal complexes. The use of azine N-oxides as starting compounds is often associated with the employment of electrophilic reagents or media. The reaction of electrophiles with azine N-oxides allows one to purposefully and selectively introduce substituents at positions 2, 3, or 4 of the azine fragment (relative to the nitrogen atom), depending on the choice of the reagent or the reaction conditions. The review considers the reactions of intramolecular nucleophilic substitution with preliminary generation of azine N-oxide adducts with electrophilic reagents, SEAr reactions, and photocatalytic reactions. Original research published over the past 5 years is covered.

Authors: Sergey V. Baykov, Vadim P. Boyarskiy*

Author Biographies

Сергей В. Байков, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

Сергей Валентинович Байков

Научный сотрудник кафедры физической органической химии

Вадим П. Боярский, Saint Petersburg State University, 7/9 Universitetskaya Embankment, Saint Petersburg 199034

Вадим Павлович Боярский

Профессор кафедрыфизической органической химии Института химии

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Published

2020-07-31

Issue

Vol. 56 No. 7 (2020): Synthesis and transformations of heterocycles under electrophilic conditions

Section

Review Articles