Palladium-Catalyzed Cross Coupling Reaction of N-Alkoxyimidoyl Bromides and Its Application to One-Pot Synthesis of N-Arylamines

• Ueda Masafumi

  Kobe Pharmaceutical University

• Sugita Shoichi

  Kobe Pharmaceutical University

• Aoi Naoki

  Kobe Pharmaceutical University

• Sato Aoi

  Kobe Pharmaceutical University

• Ikeda Yuki

  Kobe Pharmaceutical University

• Ito Yuta

  Kobe Pharmaceutical University

• Miyoshi Tetsuya

  Kobe Pharmaceutical University

• Naito Takeaki

  Kobe Pharmaceutical University

• Miyata Okiko

  Kobe Pharmaceutical University

Bibliographic Information

Other Title

• Communication to the editor: Palladium-catalyzed cross coupling reaction of N-alkoxyimidoyl bromides and its application to one-pot synthesis of N-arylamines

Abstract

The synthetic utility of N-alkoxyimidoyl halides is demonstrated using the palladium-catalyzed cross-coupling reaction. The Sonogashira and Suzuki–Miyaura coupling reactions of N-alkoxyimidoyl bromides produced versatile ketoxime ethers in good to excellent yields. A one-pot reaction of the imidoyl bromides with arylboronic acid and allylmagnesium bromide to produce N-arylamines via Suzuki–Miyaura coupling followed by domino reaction involving sequential addition-eliminative rearrangement-addition reactions was developed.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 59 (9), 1206-1208, 2011

  The Pharmaceutical Society of Japan

Keywords

• imidoyl bromide
• Suzuki–Miyaura coupling
• Sonogashira coupling
• one-pot reaction
• <i>N</i>-arylamine

Details

• CRID: 1390001204173404800
• NII Article ID: 130001852331
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.59.1206
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 11217096
• PubMed: 21881275
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I11217096
• Web Site: http://www.jstage.jst.go.jp/article/cpb/59/9/59_9_1206/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • PubMed
  • CiNii Articles
• Abstract License Flag: Disallowed