California Institute of Technology

Myles Benton Herbert

Robert H Grubbs

Benjamin Keith Keitz

Koji Endo

Vanessa M Marx

Zachary K Wickens

Paresma Rasiklal Patel

Lauren E Rosebrugh

The invention relates to C&#x2014;H activated olefin metathesis catalyst compounds, the preparation of such compounds, and the use of such catalysts in the metathesis of olefins and olefin compounds, more particularly, the use of such catalysts in Z selective olefin metathesis reactions. In general, the catalyst compounds of the invention comprise a Group 8 metal (M), an alkylidene moiety (&#x2550;CRR), or more generally (&#x2550;(C)CRR), an anionic ligand (X), two or three neutral ligands (L, L, and L) and a 2-electron anionic donor bridging moiety (Q*) that forms a chelate ring structure in conjunction with L1 and M. Such catalysts generally correspond to the formula X(L)LLQ*M=(C)CRR, wherein X1 is any anionic ligand, L, L, and Lare, independently, any neural electron donor ligand, k is 0 or 1, m is 0, 1, or 2, Q* is a 2-electron anionic donor bridging moiety linking Land M, M is a Group 8 transition metal, and Rand Rare, independently, hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, substituted heteroatom-containing hydrocarbyl, or functional groups. The invention has utility in the fields of catalysis, organic synthesis, polymer chemistry, and industrial and fine chemicals chemistry.

Z-selective olefin metathesis catalysts and their synthetic procedure

A novel chelated ruthenium-based metathesis catalyst bearing an N-2,6-diisopropylphenyl group is reported and displays near-perfect selectivity for the Z-olefin (&#x3e;95%), as well as unparalleled TONs of up to 7,400, in a variety of homodimerization and industrially relevant metathesis reactions. This derivative and other new catalytically-active species were synthesized using an improved method employing sodium carboxylates to induce the salt metathesis and C&#x2014;H activation of these chelated complexes. All of these new ruthenium-based catalysts are highly Z-selective in the homodimerization of terminal olefins.

Z-selective metathesis catalysts

The present invention is directed to methods of synthesizing insect pheromones, particularly lepidopteran insect pheromones, their precursors and derivatives from inexpensive, readily available starting materials using olefin metathesis catalysis.

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Pasadena, CA, United States of America

Myles Benton Herbert