Work

A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines

Year: 2019

Type: article

Abstract: We report that HCl·DMPU induces the formation of (thiomethyl)methyl carbenium ion from DMSO under mild conditions. Homoallylic amines react with this electrophile to generate 4-chloropiperidines in good yields. The method applies to both aromatic and aliphatic amines. The use of HCl·DMPU as both non-nucleophilic base and chloride source constitutes an environmentally benign alternative for piperidine formation. The reaction has a broad substrate scope, and the conditions offer good chemical yields with high functional group tolerance and scalability.

Source: The Journal of Organic Chemistry

DOI: 10.1021/acs.joc.8b03162

Authors: Rene Ebule, Sagar Mudshinge, Michael H. Nantz, Mark S. Mashuta, Gerald B. Hammond, Bo Xu

Institutions: University of Louisville, Donghua University

Language: English

Topic: Organic and Inorganic Chemical Reactions

Subfield: Spectroscopy

Field: Chemistry

Domain: Physical Sciences

Open Access status: green

Funders: National Natural Science Foundation of China, National Institute of General Medical Sciences

Awards: G569018084, Nucleophilic halogenation reagents