Sterically Tuned N-Heterocyclic Carbene Ligands for the Efficient Formation of Hindered Products in Ru-Catalyzed Olefin Metathesis.

Content Provider	Europe PMC
Author	Planer, Sebastian Małecki, Paweł Trzaskowski, Bartosz Kajetanowicz, Anna Grela, Karol
Copyright Year	2020
Abstract	Formationof tetrasubstituted C–C double bonds via olefinmetathesis is considered very challenging for classical Ru-based complexes.In the hope to improve this condition, three ruthenium olefin metathesiscatalysts bearing sterically reduced N-heterocycliccarbene (NHC) ligands with xylyl “arms” were synthesized,characterized using both computational and experimental techniques,and tested in a number of challenging reactions. The catalysts arepredicted to initiate much faster than the analogue with mesityl N-substituents. We also foreboded the rotation of xylylside groups at ambient temperature and the existence of all four atropoisomersin the solution, which was in agreement with experimental data. Thesecatalysts exhibited high activity at relatively low temperatures (45–60°C) and at reduced catalyst loadings in various reactions ofsterically hindered alkenes, including complex polyfunctional substratesof pharmaceutical interest, such as yangonin precursors, chrysantemicacid derivatives, analogues of cannabinoid agonists, α-terpineol,and finally a thermally unstable peroxide.
Related Links	https://europepmc.org/backend/ptpmcrender.fcgi?accid=PMC7587146&blobtype=pdf
Journal	ACS Catalysis [ACS Catal]
Volume Number	10
DOI	10.1021/acscatal.0c02770
PubMed Central reference number	PMC7587146
Issue Number	19
PubMed reference number	33123411
e-ISSN	21555435
Language	English
Publisher	AmericanChemical Society
Publisher Date	2020-09-18
Access Restriction	Open
Rights License	This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
Subject Keyword	olefin metathesis ruthenium ligands sterically reduced N-heterocyclic carbenes catalysis tetrasubstituted double bonds
Content Type	Text
Resource Type	Article
Subject	Chemistry Catalysis