Approach to vicinal t-Boc-amino dibromides via catalytic aminobromination of nitrostyrenes without using chromatography and recrystallization

Hao Sun, Jianlin Han, Padmanabha V. Kattamuri, Yi Pan, Guigen Li

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

Abstract

A 1.0 mol % amount of K3PO4·3H2O was found to catalyze aminohalogenation reaction of nitrostyrenes with N,N-dibromo-tert-butylcarbamate (t-Boc-NBr2) in a dichloroethane system. Good to excellent yields and complete regioselectivity have been achieved by taking advantage of the GAP workup without using traditional purification techniques such as column chromatography and recrystallization. Anew mechanism is proposed involving radical and ionic catalytic cycles and an intramolecular migration.

Original languageEnglish
Pages (from-to)1171-1175
Number of pages5
JournalJournal of Organic Chemistry
Volume78
Issue number3
DOIs
StatePublished - Feb 1 2013

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