Arene vs. Alkene Substrates in Ru‐Catalyzed Olefin Metathesis: a DFT Investigation. Issue 30 (16th July 2020)

• Record Type: Journal Article
• Authors: Poater, Albert; D'Alterio, Massimo Christian; Talarico, Giovanni; Chauvin, Remi
• Is Part Of: European journal of organic chemistry. Issue 30(2020)
• Page Start: 4743
• Page End: 4749
• Publication Date: 2020-07-16
• Subjects: Pyran -- Aromaticity -- Olefin metathesis -- Metallacycles -- Ruthenium; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000725
• Languages: English
• ISSNs: 1434-193X

Abstract

Abstract : DFT calculations have been performed to compare metathesis of olefin, diene, and arene substrates catalyzed by a 2 nd generation Ru(SIMes)‐based complex. A large screening of modified substrates has been performed with the intention to explore the energetic gaps between acyclically conjugated alkenes and arenes in metathesis processes. The results are analyzed through the effects of conjugation vs. aromaticity, as quantified by the HOMA and NICS aromaticity indices, as well as the effects of non‐covalent interactions between coplanar rings and/or any ring with functional groups nearby. Abstract : Why olefin metathesis by Grubbs catalysts is not valid for aromatic arene substrates? DFT calculations, aromaticity indices, as well as the effects of non‐covalent interactions between rings provide the solution.