Direct Aryl C−H Amination with Primary Amines Using Organic Photoredox Catalysis

Margrey, Kaila A.; Levens, Alison; Nicewicz, David A.

doi:10.1002/anie.201709523

Direct Aryl C−H Amination with Primary Amines Using Organic Photoredox Catalysis

Journal Article · Mon Nov 13 00:00:00 EST 2017 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201709523· OSTI ID:1408542

Margrey, Kaila A. ^[1]; Levens, Alison ^[1]; ^[1]

Department of Chemistry University of North Carolina at Chapel Hill Chapel Hill NC 27599-3290 USA

Abstract

The direct catalytic C−H amination of arenes is a powerful synthetic strategy with useful applications in pharmaceuticals, agrochemicals, and materials chemistry. Despite the advances in catalytic C−H functionalization, the use of aliphatic amine coupling partners is limited. Described herein is the construction of C−N bonds, using primary amines, by direct C−H functionalization with an acridinium photoredox catalyst under an aerobic atmosphere. A wide variety of primary amines, including amino acids and more complex amines are competent coupling partners. Various electron‐rich aromatics and heteroaromatics are useful scaffolds in this reaction, as are complex, biologically active arenes. We also describe the ability to functionalize arenes that are not oxidized by an acridinium catalyst, such as benzene and toluene, thus supporting a reactive amine cation radical intermediate.

View Accepted Manuscript (Publisher)

Sponsoring Organization:: USDOE

Grant/Contract Number:: SC0001011

OSTI ID:: 1408542

Alternate ID(s):: OSTI ID: 1537461

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 49 Vol. 56; ISSN 1433-7851

Publisher:: Wiley Blackwell (John Wiley & Sons)Copyright Statement

Country of Publication:: Germany

Language:: English

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