Efficient [(NHC)Au(NTf₂)]-catalyzed hydrohydrazidation of terminal and internal alkynes

• Maximillian Heidrich and
• Herbert Plenio

Beilstein J. Org. Chem. 2020, 16, 2080–2086, doi:10.3762/bjoc.16.175

• Maximillian Heidrich Herbert Plenio Organometallic Chemistry, Technische Universität Darmstadt, Alarich-Weiss-Str. 12, 64287 Darmstadt, Germany 10.3762/bjoc.16.175 Abstract The efficient hydrohydrazidation of terminal (6a–r, 18 examples, 0.1–0.2 mol % [(NHC)Au(NTf2)], T = 60 °C) and internal

• alkynes (7a–j, 10 examples, 0.2–0.5 mol % [(NHC)Au(NTf2)], T = 60–80 °C) utilizing a complex with a sterically demanding bispentiptycenyl-substituted NHC ligand and the benign reaction solvent anisole, is reported. Keywords: alkyne; gold; homogeneous catalysis; hydrohydrazidation; NHC ligand

• activity of gold complexes in such reactions tends to be higher, when using sterically demanding ligands (NHC, phosphine) [41]. Recently, the hydrohydrazidation of substituted phenylacetylenes using [(Ph3P)Au(NTf2)] as the catalyst was reported by Rassadin, Kukushkin et al. [42]. Catalyst loadings of 6 mol