Z-Selective (Cross-)Dimerization of Terminal Alkynes Catalyzed by an Iron Complex

Orestes Rivada-Wheelaghan, Subrata Chakraborty, Linda J W Shimon, Yehoshoa Ben-David, David Milstein

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

Efficient iron-catalyzed homocoupling of terminal alkynes and cross-dimerization of aryl acetylenes with trimethylsilylacetylene is reported. The complex [Fe(H)(BH4)(iPr-PNP)] (1) catalyzed the (cross-)dimerization of alkynes at room temperature, with no need for a base or other additives, to give the corresponding dimerized products with Z selectivity in excellent yields (79-99 %). Ironing out the kinks: Iron-catalyzed homocoupling of terminal alkynes and cross-dimerization of aryl acetylenes with a silylacetylene avoided problems of precious metal catalysis, usage of additives, and selectivity issues encountered with other catalysts in the past. The complex [Fe(H)(BH4)(iPr-PNP)] (1) operated efficiently at room temperature without a base or other additives to give the corresponding products with Z selectivity in 79-99 % yield (see scheme).

Original languageEnglish
Pages (from-to)6942-6945
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number24
DOIs
Publication statusPublished - Jun 6 2016

Fingerprint

Alkynes
Dimerization
Iron
Acetylene
Catalyst selectivity
Precious metals
Catalysis
Temperature
Catalysts

Keywords

  • C-C coupling
  • homogeneous catalysis
  • hydroalkynylation
  • iron
  • pincer complexes

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis

Cite this

Z-Selective (Cross-)Dimerization of Terminal Alkynes Catalyzed by an Iron Complex. / Rivada-Wheelaghan, Orestes; Chakraborty, Subrata; Shimon, Linda J W; Ben-David, Yehoshoa; Milstein, David.

In: Angewandte Chemie - International Edition, Vol. 55, No. 24, 06.06.2016, p. 6942-6945.

Research output: Contribution to journalArticle

Rivada-Wheelaghan, Orestes ; Chakraborty, Subrata ; Shimon, Linda J W ; Ben-David, Yehoshoa ; Milstein, David. / Z-Selective (Cross-)Dimerization of Terminal Alkynes Catalyzed by an Iron Complex. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 24. pp. 6942-6945.
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