No Transition Metals Required - Oxygen Promoted Synthesis of Imines from Primary Alcohols and Amines Under Ambient Conditions

Overview

Journal Chemistry

Specialty Chemistry

Date 2023 Mar 3

PMID 36866600

Authors

Daniel Himmelbauer

Radu Talmazan

Stefan Weber

Jan Pecak

Antonio Thun-Hohenstein

Maxine-Sophie Geissler

Lukas Pachmann

Marc Pignitter

Maren Podewitz

Karl Kirchner

Affiliations

Soon will be listed here.

Abstract

The synthesis of imines denotes a cornerstone in organic chemistry. The use of alcohols as renewable substituents for carbonyl-functionality represents an attractive opportunity. Consequently, carbonyl moieties can be in situ generated from alcohols upon transition-metal catalysis under inert atmosphere. Alternatively, bases can be utilized under aerobic conditions. In this context, we report the synthesis of imines from benzyl alcohols and anilines, promoted by KO Bu under aerobic conditions at room temperature, in the absence of any transition-metal catalyst. A detailed investigation of the radical mechanism of the underlying reaction is presented. This reveals a complex reaction network fully supporting the experimental findings.

Citing Articles

No Transition Metals Required - Oxygen Promoted Synthesis of Imines from Primary Alcohols and Amines under Ambient Conditions.

Himmelbauer D, Talmazan R, Weber S, Pecak J, Thun-Hohenstein A, Geissler M Chemistry. 2023; 29(29):e202300094.

PMID: 36866600 PMC: 10946877. DOI: 10.1002/chem.202300094.

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