Rhodium(III) Iodide Catalyzed Carboamination of Alkynes through C–N Bond Activation

Author:

Xu Tao12ORCID,Li XinXin1,Yang Qingxing1,Zhang Yuna1

Affiliation:

1. Molecular Synthesis Center and Key Laboratory of Marine Drugs, Ministry of Education; School of Medicine and Pharmacy, Ocean University of China

2. Laboratory for Marine Drugs and Bioproducts, Pilot National Laboratory for Marine Science and Technology

Abstract

AbstractHere, we report a RhI3-catalyzed intramolecular carboamination reaction to access polysubstituted indoles. The protocol features a broad substrate scope (>20 examples), good functional-group compatibility, and a low catalyst loading (5 mol% Rh). Good to excellent yields (up to 98%) were obtained. An unprecedented C–N bond-cleavage mode via a six-membered transition state σ-bond metathesis mechanism was proposed based on control experiments. A series of C3-allylated indole derivatives were accessed, proving that the system provides an alternative catalytic route to polysubstituted indoles.

Funder

National Science Foundation of China

Natural Science Fund for Distinguished Young Scholars of Shandong Province

Fundamental Research Funds for the Central Universities

Marine S&T Fund of Shandong Province

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry

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