Electrochemical Hofmann rearrangement mediated by NaBr: practical access to bioactive carbamates.

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Abstract

An electrochemical Hofmann rearrangement is reported. With the mediation of NaBr, highly corrosive and toxic halogens are avoided. Moreover, this efficient and green approach is well compatible with a broad range of amides, including several commercial medicine derivatives, and provides direct access to synthetically useful carbamates. The synthetic utility of this method is also demonstrated by the preparation of 15N labeling carbamate and gram-scale synthesis of Amantadine.

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Journal

Journal ID (iso-abbrev): Org Biomol Chem

Title: Organic & biomolecular chemistry

Publisher: Royal Society of Chemistry (RSC)

ISSN (Electronic): 1477-0539

ISSN (Print): 1477-0520

Publication date (Electronic): July 07 2018

Volume: 16

Issue: 25

Affiliations

[1 ] College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, 473061, P. R. China. xukun@nynu.edu.cn shengzhang@nynu.edu.cn.

Article

DOI: 10.1039/c8ob01059e

PubMed ID: 29900466

SO-VID: c7a421a2-9089-45f0-a136-a4042770a020

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