Display options
Share it on

Tetrahedron Lett. 2013 Feb 01;54(9):1141-1144. doi: 10.1016/j.tetlet.2012.12.047.

A novel route to organonitrites by Pd-catalyzed cross-coupling of sodium nitrite and potassium organotrifluoroborates.

Tetrahedron letters

Mohammad Al-Masum, Nabil Saleh, Tasfia Islam

Affiliations

  1. Department of Chemistry, Tennessee State University, 3500 John A. Merritt Blvd., Nashville, TN 37209, United States.

PMID: 24926109 PMCID: PMC4051233 DOI: 10.1016/j.tetlet.2012.12.047

Abstract

Microwave irradiated palladium-catalyzed cross-coupling reaction of potassium styryltrifluoroborates and sodium nitrite gives the corresponding styryl nitrites in high yields. Potassium aryltrifluoroborates also furnish aryl nitrites under same reaction condition. This unprecedented cross-coupling is an interesting development and has the potential to lead to new nitration protocols.

Keywords: Microwave; Organonitrites; Organotrifluoroborates; Sodium nitrite in cross-coupling

References

  1. Org Lett. 2006 May 11;8(10):2031-4 - PubMed
  2. Org Lett. 2006 Jan 5;8(1):11-3 - PubMed
  3. Chem Rev. 1996 Dec 19;96(8):3241-3268 - PubMed
  4. J Am Chem Soc. 2009 Sep 16;131(36):12898-9 - PubMed
  5. J Am Chem Soc. 2006 Jun 28;128(25):8150-1 - PubMed
  6. Acc Chem Res. 2007 Apr;40(4):275-86 - PubMed
  7. Chem Rev. 2008 Jan;108(1):288-325 - PubMed

Publication Types

Grant support