Synthesis of Polysubstituted Pyrroles via Silver-Catalyzed Oxidative Radical Addition of Cyclopropanols to Imines
Authors:
- 11 September 2020
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 22 (19) , 7542-7546
Abstract
A silver-catalyzed formal [3 + 2] cycloaddition reaction, with cyclopropanols as a C3 subunit and imines as a two-atom subunit, is developed. The reaction takes place under mild conditions and produces a broad array of polysubstituted pyrroles in medium to high yields. It represents the first example of oxidative radical addition to imines, thus offering a new choice for the direct C–H functionalization of imines.Keywords
Funding Information
- National Natural Science Foundation of China (21672191)
- Natural Science Foundation of Zhejiang Province (LZ20B020001)
This publication has 68 references indexed in Scilit:
- Alkyl Radical Addition to Aliphatic and Aromatic N-Acylhydrazones Using an Organic Photoredox CatalystOrganic Letters, 2019
- Inter- and Intramolecular Carbon-Carbon Bond-Forming Radical ReactionsSynlett, 2012
- Carbon-Carbon Bond Construction Based on Radical Addition to C=N BondSynlett, 2004
- Enantioselective Radical Addition to N‐Acyl Hydrazones Mediated by Chiral Lewis AcidsAngewandte Chemie International Edition, 2003
- Enantioselective Radical ProcessesChemical Reviews, 2003
- Addition of carbon-centered radicals to imines and related compoundsTetrahedron, 2001
- Photoinduced Formation of β-Oxy-α,α-disubstituted-α-amino Acid Derivatives from KetoximesOrganic Letters, 2001
- Highly Stereoselective Intermolecular Radical Addition to Aldehyde Hydrazones from a Chiral 3-Amino-2-oxazolidinoneJournal of the American Chemical Society, 2000
- Use of Lewis Acids in Free Radical ReactionsAngewandte Chemie International Edition, 1998
- Tandem Radical Reactions of Carbon Monoxide, Isonitriles, and Other Reagent Equivalents of the Geminal Radical Acceptor/Radical Precursor SynthonChemical Reviews, 1996