Regioselective acceptorless dehydrogenative coupling of N-heterocycles toward functionalized quinolines, phenanthrolines, and indoles

Angewandte Chemie
Dinesh TalwarJianliang Xiao

Abstract

A new strategy has been developed for the oxidant- and base-free dehydrogenative coupling of N-heterocycles at mild conditions. Under the action of an iridium catalyst, N-heterocycles undergo multiple sp(3) CH activation steps, generating a nucleophilic enamine that reacts in situ with various electrophiles to give highly functionalized products. The dehydrogenative coupling can be cascaded with Friedel-Crafts addition, resulting in a double functionalization of the N-heterocycles.

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Citations

Feb 1, 2017·Journal of the American Chemical Society·Shota KatoMotomu Kanai
Aug 20, 2016·Angewandte Chemie·Masahiro Kojima, Motomu Kanai
Mar 11, 2017·Chemical Communications : Chem Comm·Chao Wang, Jianliang Xiao
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Jun 13, 2015·Organic & Biomolecular Chemistry·Xiang SunMing Yan
Jan 9, 2020·Organic & Biomolecular Chemistry·Milanpreet Kaur, Jeffrey F Van Humbeck
Sep 26, 2015·Chemistry : a European Journal·Hsin-Yi Tiffany ChenJianliang Xiao
Feb 2, 2021·The Journal of Organic Chemistry·Xinyuan LiuJiajing Tan
Mar 30, 2021·ChemCatChem·Holly Jane DavisYasunori Okamoto
Jun 25, 2021·Chemical Science·Jungwon KimSoon Hyeok Hong
Sep 28, 2017·Chemical Reviews·Akshai KumarAlan S Goldman
Aug 7, 2019·Journal of the American Chemical Society·Wei MaChao Wang
May 6, 2020·The Journal of Organic Chemistry·Ruchun YangHu Cai
Aug 2, 2018·Organic Letters·Nadine ZumbrägelHarald Gröger

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