Cationic Iridium-Catalyzed Synthesis Initiated by the Cleavage of C-H, N-H, and C-O Bonds

• Shibata Takanori

  Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University JST, ACT-C

• Tsuchikama Kyoji

  Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University

• Pan Shiguang

  Department of Chemistry and Biochemistry, School of Advanced Science and Engineering, Waseda University

Abstract

The direct functionalization of inactive bonds is an ideal transformation in organic synthesis because the introduction of activating groups, such as halogens and metals, to substrates is unnecessary and by-products derived from them are not formed. This report describes several types of cationic iridium-catalyzed reactions that occur through C-H, N-H, or C-O bond cleavage. The carbonyl-directed sp² C-H bond activation of aryl ketones realized new approaches to benzofulvene, benzofuran and indole synthesis, as well as the C2-position-selective alkylation of N-acyl-protected indoles. The enantioselective sp³ C-H alkylation of 2-(alkylamino)pyridines and the intermolecular enantioselective hydroamination of heteroaromatic amines gave various chiral amines. O-to-N-alkyl migration in 2-alkoxypyridines gave N-alkylpyridones via C-O bond cleavage.

Journal

• Journal of Synthetic Organic Chemistry, Japan

  Journal of Synthetic Organic Chemistry, Japan 71 (11), 1182-1194, 2013

  The Society of Synthetic Organic Chemistry, Japan

Keywords

• Organic Chemistry

Details

• CRID: 1390001205341643904
• NII Article ID: 130003385858
• NII Book ID: AN0024521X
• DOI: 10.5059/yukigoseikyokaishi.71.1182
• COI: 1:CAS:528:DC%2BC3sXhvVyhur%2FI
• ISSN: 18836526
• ISSN: 00379980
• NDL BIB ID: 024989644
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I024989644
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
• Abstract License Flag: Disallowed