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Ruthenium(0)-catalyzed cross-coupling of aryl methyl ethers with organoboranes by selective C–O cleavage

https://doi.org/10.1039/D3QO00042G

Zhang, Jin; Wang, Xin; Liu, Jiale; Wang, Xiaogang; Yang, Xinkan; Zhao, Qun; Ma, Yangmin; Fang, Ran; Szostak, Michal (March 2023, Organic Chemistry Frontiers)

The activation of C–O bonds in aryl methyl ethers is a fundamental method for the cross-coupling of carbon–oxygen bonds; however, this process is highly challenging due to the high dissociation energy compared with other phenol derivatives. Herein, we report a mild Ru(0)-catalyzed cleavage of C(aryl)–O bonds enabled by a combination of a Ru 3 (CO) 12 catalyst and an imine auxiliary. This method offers rapid entry to synthetically valuable biaryl aldehydes from abundant anisoles. Broad functional group tolerance is observed using this strategy, including unprecedented tolerance towards aryl bromides. The synthetic utility of this strategy has been demonstrated in sequential processes to construct complex biaryls, exploiting the orthogonal selectivity of C–O bond activation. DFT studies were conducted to provide insight into the selectivity of C–O bond cleavage. This method establishes the mildest approach to C–OMe cross-coupling reported to date.
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Ruthenium-Catalyzed C–F Bond Arylation of Polyfluoroarenes: Polyfluorinated Biaryls by Integrated C–F/C–H Functionalization

https://doi.org/10.1021/acscatal.2c04401

Zhang, Jin; Liu, Jiale; Wang, Xiaogang; Yang, Xinkan; Ma, Yangmin; Fang, Ran; Zhao, Qun; Szostak, Michal (November 2022, ACS Catalysis)

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A 3-D constitutive model for finite element analyses of agarose with a range of gel concentrations

https://doi.org/10.1016/j.jmbbm.2020.104150

Wang, Xiaogang; June, Ronald K.; Pierce, David M. (February 2021, Journal of the Mechanical Behavior of Biomedical Materials)
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Synthesis of C6-Substituted Isoquinolino[1,2- b ]quinazolines via Rh(III)-Catalyzed C–H Annulation with Sulfoxonium Ylides

https://doi.org/10.1021/acs.joc.9b03065

Zhang, Jin; Wang, Xiaogang; Chen, Di; Kang, Yifan; Ma, Yangmin; Szostak, Michal (March 2020, The Journal of Organic Chemistry)

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Advances toward multiscale computational models of cartilage mechanics and mechanobiology

https://doi.org/10.1016/j.cobme.2019.09.013

Wang, Xiaogang; Neu, Corey P.; Pierce, David M. (September 2019, Current Opinion in Biomedical Engineering)

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Ruthenium(II)-Catalyzed Ortho -C–H Alkylation of Naphthylamines with Diazo Compounds for Synthesis of 2,2-Disubstituted π-Extended 3-Oxindoles in Water

https://doi.org/10.1021/acs.orglett.0c01811

Wang, Xiaogang; Zhang, Jin; He, Yuan; Chen, Di; Wang, Chao; Yang, Fangzhou; Wang, Weitao; Ma, Yangmin; Szostak, Michal (July 2020, Organic Letters)
null (Ed.)
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Rh(III)-Catalyzed C–H Amidation of 2-Arylindoles with Dioxazolones: A Route to Indolo[1,2- c ]quinazolines

https://doi.org/10.1021/acs.orglett.9b02615

Wang, Xiaogang; Zhang, Jin; Chen, Di; Wang, Bo; Yang, Xiufang; Ma, Yangmin; Szostak, Michal (August 2019, Organic Letters)

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On incorporating osmotic prestretch/prestress in image-driven finite element simulations of cartilage

https://doi.org/10.1016/j.jmbbm.2018.06.014

Wang, Xiaogang; Eriksson, Thomas S.E.; Ricken, Tim; Pierce, David M. (October 2018, Journal of the Mechanical Behavior of Biomedical Materials)

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