Concepedia

Metal-free nitro-carbocyclization of activated alkenes: a direct approach to synthesize oxindoles by cascade C–N and C–C bond formation

Tao Shen, Yizhi Yuan, Ning Jiao

Chemical Communications · 2013 · 174 citations · 40 references

DOI

Concepts

Abstract

A novel and direct metal-free nitro-carbocyclization of activated alkenes leading to valuable nitro-containing oxindoles via cascade C-N and C-C bond formation has been developed. The mechanistic study indicates that the initial NO and NO2 radical addition and the following C-H functionalization processes are involved in this transformation.

References

40

Catalytic Asymmetric Synthesis of Oxindoles Bearing a Tetrasubstituted Stereocenter at the C‐3 Position

Feng Zhou, Yun‐Lin Liu, Jian Zhou · Advanced Synthesis & Catalysis · 2010 · 1.2K citations

, , +12

Asymmetric Syntheses of Oxindole and Indole Spirocyclic Alkaloid Natural Products

Barry M. Trost, Megan K. Brennan · Synthesis · 2009 · 1.1K citations

, , +12

An efficient organocatalytic method for constructing biaryls through aromatic C–H activation

Chang‐Liang Sun, Hu Li, Da‐Gang Yu et al. · Nature Chemistry · 2010 · 648 citations

, , +13

Direct Annulations toward Phosphorylated Oxindoles: Silver‐Catalyzed Carbon‐Phosphorus Functionalization of Alkenes

Ya‐Min Li, Meng Sun, Hongli Wang et al. · Angewandte Chemie International Edition · 2013 · 427 citations · Full text

, , +5

Synthesis of Oxindoles by Iron‐Catalyzed Oxidative 1,2‐Alkylarylation of Activated Alkenes with an Aryl C(sp<sup>2</sup>)H Bond and a C(sp<sup>3</sup>)H Bond Adjacent to a Heteroatom

Wen‐Ting Wei, Mingbo Zhou, Jian‐Hong Fan et al. · Angewandte Chemie International Edition · 2013 · 400 citations

, , +14