Rene Ebule1, Sagar Mudshinge1, Michael H Nantz1, Mark S Mashuta1, Gerald B Hammond1, Bo Xu2. 1. Department of Chemistry , University of Louisville , Louisville , Kentucky 40292 , United States. 2. College of Chemistry, Chemical Engineering and Biotechnology , Donghua University , 2999 North Renmin Lu , Shanghai 201620 , China.
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.
We report that HCl·n class="Chemical">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.