Premium
Stereoselective Alkyne Hydrogenation by using a Simple Iron Catalyst
Author(s) -
Gregori Bernhard J.,
Schwarzhuber Felix,
Pöllath Simon,
Zweck Josef,
Fritsch Lorena,
Schoch Roland,
Bauer Matthias,
Jacobi von Wangelin Axel
Publication year - 2019
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201900926
Subject(s) - catalysis , alkyne , stereoselectivity , chemistry , metal , hydride , heterogeneous catalysis , noble metal , combinatorial chemistry , organic chemistry , inorganic chemistry
Abstract The stereoselective hydrogenation of alkynes constitutes one of the key approaches for the construction of stereodefined alkenes. The majority of conventional methods utilize noble and toxic metal catalysts. This study concerns a simple catalyst comprised of the commercial chemicals iron(II) acetylacetonate and diisobutylaluminum hydride, which enables the Z ‐selective semihydrogenation of alkynes under near ambient conditions (1–3 bar H 2 , 30 °C, 5 mol % [Fe]). Neither an elaborate catalyst preparation nor addition of ligands is required. Mechanistic studies (kinetic poisoning, X‐ray absorption spectroscopy, TEM) strongly indicate the operation of small iron clusters and particle catalysts.