Nonafluorobutanesulfonyl Azide as a Shelf-Stable Highly Reactive Oxidant for the Copper-Catalyzed Synthesis of 1,3-Diynes from Terminal Alkynes

  1. José Ramón Suárez 1
  2. Daniel Collado-Sanz 2
  3. Diego J. Cárdenas 2
  4. Jose Luis Chiara 1
  1. 1 Instituto de Química Orgánica General (IQOG-CSIC), Juan de la Cierva 3, 28006 Madrid, Spain
  2. 2 Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Campus de Cantoblanco, 28049 Madrid, Spain
Aldizkaria:
Journal of Organic Chemistry

ISSN: 0022-3263,  1520-6904

Argitalpen urtea: 2015

Alea: 80

Zenbakia: 2

Orrialdeak: 1098-1106

Mota: Artikulua

DOI: 10.1021/JO5025909 GOOGLE SCHOLAR lock_openSarbide irekia editor

Beste argitalpen batzuk: Journal of Organic Chemistry

Laburpena

Nonafluorobutanesulfonyl azide is a highly efficient reagent for the copper-catalyzed coupling of terminal alkynes to give symmetrical and unsymmetrical 1,3-diynes in good to excellent yields and with good functional group compatibility. The reaction is extremely fast (<10 min), even at low temperature (−78 °C), and requires substoichiometric amounts of a simple copper(I) or copper(II) salt (2–5 mol %) and an organic base (0.6 mol %). A possible mechanistic pathway is briefly discussed on the basis of model DFT theoretical calculations. The quantitative assessment of the safety of use and shelf stability of nonafluorobutanesulfonyl azide has confirmed that this reagent is a superior and safe alternative to other electrophilic azide reagents in use today.

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