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

Author:

Himmelbauer Daniel1,Talmazan Radu2ORCID,Weber Stefan1ORCID,Pecak Jan1ORCID,Thun‐Hohenstein Antonio1,Geissler Maxine‐Sophie1,Pachmann Lukas1,Pignitter Marc3ORCID,Podewitz Maren2ORCID,Kirchner Karl1ORCID

Affiliation:

1. Institute of Applied Synthetic Chemistry TU Wien Getreidemarkt 9/163-AC A-1060 Wien Austria

2. Institute of Materials Chemistry TU Wien Getreidemarkt 9 A-1060 Wien Austria

3. Department of Physiological Chemistry Faculty of Chemistry University of Vienna Althanstrasse 14 1090 Wien Austria

Abstract

AbstractThe 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 KOtBu 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.

Funder

Austrian Science Fund

Publisher

Wiley

Subject

General Chemistry,Catalysis,Organic Chemistry

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