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A 3,4-dimercapto-3-cyclobutene-1,2-dione-chelated Ruthenium Carbene Catalyst for Z-stereoretentive/stereoselective Olefin Metathesis

A 3,4-dimercapto-3-cyclobutene-1,2-dione-chelated Ruthenium Carbene Catalyst for Z-stereoretentive/stereoselective Olefin Metathesis

Tao Wang, Qingxiao Xie, Weijie Guo, Shutao Wu, Huiqing Zhang, Jianhui Wang, Botao Wu

Dalton Trans. 2019 May 15;48(19):6473-6483.

PMID: 30993295

Abstract:

A ruthenium carbene catalyst chelated with a 3,4-dioxocyclobut-1-ene-1,2-dithiolate ligand was synthesized and its molecular structure was determined by single-crystal X-ray diffraction. The Ru catalyst had excellent catalytic activity with high yields and good Z/E ratios for the ring opening metathesis polymerization (ROMP) of norbornene (yield: 96%/Z/E: 86 : 14) and 1,5-cyclooctadiene (yield: 86%/Z/E: 91 : 9) and for ring opening cross metathesis (ROCM) reactions of norbornene/5-norbornene-2-exo, 3-exo-dimethanol with styrene (yields: 64%-92%/Z/E: 97 : 3-98 : 2) or 4-fluorostyrene (yield: 46%-94%/Z/E: 98 : 2). The catalyst also had high Z-stereoretentivity (91 : 9-98 : 2) for cross-metathesis (CM) reactions of terminal olefins with (Z)-2-butene-1,4-diol. More importantly, the catalyst had moderate Z-stereoselectivity for homometathesis reactions of terminal olefins giving cis-olefins as the major products (Z/E ratios of 70 : 30-77 : 23). Like other Ru carbene complexes, the catalyst tolerates many different functional groups. The presented data, supported by DFT calculations, show that our catalyst, bearing a chelating 3,4-dioxocyclobut-1-ene-1,2-dithiolate ligand, exhibits higher stability towards air than Hoveyda's stereoretentive complex systems.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP699956	5-Norbornene-2-exo,3-exo-dimethanol		699-95-6	Price

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