Microwave-assisted deacylation of unactivated amides using ammonium-salt-accelerated transamidation

Yuhei Shimizu, Hiroyuki Morimoto, Ming Zhang, Takashi Ohshima

Research output: Contribution to journalArticle

44 Citations (Scopus)

Abstract

Easy does it! The chemoselective oxidative ?-C(sp3)H alkylation/cyclization reaction of N-benzyl carbamates using simple mono-, di-, and trisubstituted olefins provides functionalized N-heterocycles such as oxazinones (see picture). A TEMPO oxoammonium salt serves as the oxidant, making it possible to carry out the reaction at low temperatures. Neither a metal catalyst nor preactivation in the ?-position to the nitrogen group are needed.

Original languageEnglish
Pages (from-to)8564-8567
Number of pages4
JournalAngewandte Chemie - International Edition
Volume51
Issue number34
DOIs
Publication statusPublished - Aug 20 2012

Fingerprint

Carbamates
Cyclization
Alkylation
Alkenes
Oxidants
Ammonium Compounds
Amides
Olefins
Nitrogen
Salts
Metals
Microwaves
Catalysts
Temperature
tempamine

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Microwave-assisted deacylation of unactivated amides using ammonium-salt-accelerated transamidation. / Shimizu, Yuhei; Morimoto, Hiroyuki; Zhang, Ming; Ohshima, Takashi.

In: Angewandte Chemie - International Edition, Vol. 51, No. 34, 20.08.2012, p. 8564-8567.

Research output: Contribution to journalArticle

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