Copper-Catalyzed\nHydroamination of 2‑Alkynylazobenzenes:\nSynthesis of 3‑Alkenyl‑2<i>H</i>‑Indazoles

A copper-catalyzed intramolecular synthesis of 3-alkenyl-2<i>H</i>-indazoles from 2-alkynylazobenzenes is described. The\nreaction proceeds in a single step via C–N bond formation and\na subsequent 1,2-hydride shift, affording products in high yields.\nDFT calculations suggest the 1,2-hydride shift as the rate-determining\nstep. Further derivatization enables functionalization of the 3-alkenyl-2<i>H</i>-indazoles.

Publication Details

Journal
Figshare
Published
2024-11-02
DOI
https://doi.org/10.1021/acs.joc.4c02144.s001
Primary Topic
Educational Robotics and Engineering
Type
article
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article

Copper-Catalyzed\nHydroamination of 2‑Alkynylazobenzenes:\nSynthesis of 3‑Alkenyl‑2H‑Indazoles

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Educational Robotics and Engineering
article

Copper-Catalyzed\nHydroamination of 2‑Alkynylazobenzenes:\nSynthesis of 3‑Alkenyl‑2H‑Indazoles

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Abstract

A copper-catalyzed intramolecular synthesis of 3-alkenyl-2<i>H</i>-indazoles from 2-alkynylazobenzenes is described. The\nreaction proceeds in a single step via C–N bond formation and\na subsequent 1,2-hydride shift, affording products in high yields.\nDFT calculations suggest the 1,2-hydride shift as the rate-determining\nstep. Further derivatization enables functionalization of the 3-alkenyl-2<i>H</i>-indazoles.

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Educational Robotics and Engineering
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Copper-Catalyzed\nHydroamination of 2‑Alkynylazobenzenes:\nSynthesis of 3‑Alkenyl‑2<i>H</i>‑Indazoles · Figshare (2024) | TGRS Research Map | TGRS