4.6 Article

Development of a New Benzylating Reagent Spontaneously Releasing Benzyl Cation Equivalents at Room Temperature

Journal

CHEMISTRY-A EUROPEAN JOURNAL
Volume 20, Issue 38, Pages 12274-12278

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201403158

Keywords

alkylation; carbocations; protecting groups; reaction mechanisms; synthetic methods

Funding

  1. Ministry of Education, Culture, Sports, Science, and Technology of Japan [23790009]
  2. JST Accelerating Utilization of University IP Program [FY2013-13406991]
  3. Grants-in-Aid for Scientific Research [25460013, 26293003, 23790009, 26670001] Funding Source: KAKEN

Ask authors/readers for more resources

A new O-benzylating reagent, that is, 4-(4,6-diphenoxy- 1,3,5-triazin-2-yl)-4-benzylmorpholinium trifluoromethanesulfonate (DPT-BM), has been developed. Benzyl cation equivalents are generated from DPT-BM by dissolving the compound in a solvent at room temperature under non-acidic conditions. The benzylation of various alcohols by using a combination of DPT-BM and magnesium oxide provided the benzyl ethers in good yields.

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