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Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization.

Beilstein journal of organic chemistry

Trost BM, Ryan MC, Rao M.
PMID: 27559366
Beilstein J Org Chem. 2016 Jun 07;12:1136-52. doi: 10.3762/bjoc.12.110. eCollection 2016.

A full account of our efforts toward an asymmetric redox bicycloisomerization reaction is presented in this article. Cyclopentadienylruthenium (CpRu) complexes containing tethered chiral sulfoxides were synthesized via an oxidative [3 + 2] cycloaddition reaction between an alkyne and an...

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Trost BM, Ryan MC, Rao M. Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization. Beilstein J Org Chem. 2016;12:1136-52doi: 10.3762/bjoc.12.110.
Trost, B. M., Ryan, M. C., & Rao, M. (2016). Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization. Beilstein journal of organic chemistry, 121136-52. https://doi.org/10.3762/bjoc.12.110
Trost, Barry M, et al. "Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization." Beilstein journal of organic chemistry vol. 12 (2016): 1136-52. doi: https://doi.org/10.3762/bjoc.12.110
Trost BM, Ryan MC, Rao M. Chiral cyclopentadienylruthenium sulfoxide catalysts for asymmetric redox bicycloisomerization. Beilstein J Org Chem. 2016 Jun 07;12:1136-52. doi: 10.3762/bjoc.12.110. eCollection 2016. PMID: 27559366; PMCID: PMC4979649.
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On the Origins of Nonradiative Excited State Relaxation in Aryl Sulfoxides Relevant to Fluorescent Chemosensing.

Journal of the American Chemical Society

Kathayat RS, Yang L, Sattasathuchana T, Zoppi L, Baldridge KK, Linden A, Finney NS.
PMID: 27809511
J Am Chem Soc. 2016 Dec 14;138(49):15889-15895. doi: 10.1021/jacs.6b00572. Epub 2016 Dec 05.

We provide herein a mechanistic analysis of aryl sulfoxide excited state processes, inspired by our recent report of aryl sulfoxide based fluorescent chemosensors. The use of aryl sulfoxides as reporting elements in chemosensor development is a significant deviation from...

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Kathayat RS, Yang L, Sattasathuchana T, et al. On the Origins of Nonradiative Excited State Relaxation in Aryl Sulfoxides Relevant to Fluorescent Chemosensing. J Am Chem Soc. 2016;138(49):15889-15895doi: 10.1021/jacs.6b00572.
Kathayat, R. S., Yang, L., Sattasathuchana, T., Zoppi, L., Baldridge, K. K., Linden, A., & Finney, N. S. (2016). On the Origins of Nonradiative Excited State Relaxation in Aryl Sulfoxides Relevant to Fluorescent Chemosensing. Journal of the American Chemical Society, 138(49), 15889-15895. https://doi.org/10.1021/jacs.6b00572
Kathayat, Rahul S, et al. "On the Origins of Nonradiative Excited State Relaxation in Aryl Sulfoxides Relevant to Fluorescent Chemosensing." Journal of the American Chemical Society vol. 138,49 (2016): 15889-15895. doi: https://doi.org/10.1021/jacs.6b00572
Kathayat RS, Yang L, Sattasathuchana T, Zoppi L, Baldridge KK, Linden A, Finney NS. On the Origins of Nonradiative Excited State Relaxation in Aryl Sulfoxides Relevant to Fluorescent Chemosensing. J Am Chem Soc. 2016 Dec 14;138(49):15889-15895. doi: 10.1021/jacs.6b00572. Epub 2016 Dec 05. PMID: 27809511.
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Visible-Light-Accelerated C-H Sulfinylation of Heteroarenes.

Angewandte Chemie (International ed. in English)

Meyer AU, Wimmer A, König B.
PMID: 27910176
Angew Chem Int Ed Engl. 2017 Jan 02;56(1):409-412. doi: 10.1002/anie.201610210. Epub 2016 Dec 02.

Heteroaromatic sulfoxides are a frequent structural motif in natural products, drugs, catalysts, and materials. We report a metal-free visible-light-accelerated synthesis of heteroaromatic sulfoxides from sulfinamides and peroxodisulfate. The reaction proceeds at room temperature with blue-light irradiation and allows the...

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Meyer AU, Wimmer A, König B. Visible-Light-Accelerated C-H Sulfinylation of Heteroarenes. Angew Chem Int Ed Engl. 2016;56(1):409-412doi: 10.1002/anie.201610210.
Meyer, A. U., Wimmer, A., & König, B. (2017). Visible-Light-Accelerated C-H Sulfinylation of Heteroarenes. Angewandte Chemie (International ed. in English), 56(1), 409-412. https://doi.org/10.1002/anie.201610210
Meyer, Andreas Uwe, et al. "Visible-Light-Accelerated C-H Sulfinylation of Heteroarenes." Angewandte Chemie (International ed. in English) vol. 56,1 (2017): 409-412. doi: https://doi.org/10.1002/anie.201610210
Meyer AU, Wimmer A, König B. Visible-Light-Accelerated C-H Sulfinylation of Heteroarenes. Angew Chem Int Ed Engl. 2017 Jan 02;56(1):409-412. doi: 10.1002/anie.201610210. Epub 2016 Dec 02. PMID: 27910176.
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Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions.

Angewandte Chemie (International ed. in English)

Annapureddy RR, Burg F, Gramüller J, Golub TP, Merten C, Huber SM, Bach T.
PMID: 33438798
Angew Chem Int Ed Engl. 2021 Mar 29;60(14):7920-7926. doi: 10.1002/anie.202016561. Epub 2021 Feb 26.

An enantioselective sulfimidation of 3-thiosubstituted 2-quinolones and 2-pyridones was achieved with a stoichiometric nitrene source (PhI=NNs) and a silver-based catalyst system. Key to the success of the reaction is the use of a chiral phenanthroline ligand with a hydrogen...

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Annapureddy RR, Burg F, Gramüller J, et al. Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions. Angew Chem Int Ed Engl. 2021;60(14):7920-7926doi: 10.1002/anie.202016561.
Annapureddy, R. R., Burg, F., Gramüller, J., Golub, T. P., Merten, C., Huber, S. M., & Bach, T. (2021). Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions. Angewandte Chemie (International ed. in English), 60(14), 7920-7926. https://doi.org/10.1002/anie.202016561
Annapureddy, Rajasekar Reddy, et al. "Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions." Angewandte Chemie (International ed. in English) vol. 60,14 (2021): 7920-7926. doi: https://doi.org/10.1002/anie.202016561
Annapureddy RR, Burg F, Gramüller J, Golub TP, Merten C, Huber SM, Bach T. Silver-Catalyzed Enantioselective Sulfimidation Mediated by Hydrogen Bonding Interactions. Angew Chem Int Ed Engl. 2021 Mar 29;60(14):7920-7926. doi: 10.1002/anie.202016561. Epub 2021 Feb 26. PMID: 33438798; PMCID: PMC8048691.
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A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents.

Organic & biomolecular chemistry

Li WZ, Wang ZX.
PMID: 34037055
Org Biomol Chem. 2021 Jun 16;19(23):5082-5086. doi: 10.1039/d1ob00840d.

Ni(PEt3)Cl2-catalyzed silylation of alkyl aryl sulfoxides with silylzinc reagents was carried out. This protocol allows alkyl aryl sulfoxides to convert to arylsilicon compounds under mild reaction conditions, tolerates a range of functional groups and is suitable for a wide...

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Li WZ, Wang ZX. A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents. Org Biomol Chem. 2021;19(23):5082-5086doi: 10.1039/d1ob00840d.
Li, W. Z., & Wang, Z. X. (2021). A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents. Organic & biomolecular chemistry, 19(23), 5082-5086. https://doi.org/10.1039/d1ob00840d
Li, Wei-Ze, and Wang, Zhong-Xia. "A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents." Organic & biomolecular chemistry vol. 19,23 (2021): 5082-5086. doi: https://doi.org/10.1039/d1ob00840d
Li WZ, Wang ZX. A nickel-catalyzed silylation reaction of alkyl aryl sulfoxides with silylzinc reagents. Org Biomol Chem. 2021 Jun 16;19(23):5082-5086. doi: 10.1039/d1ob00840d. PMID: 34037055.
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Lewis acid-assisted Ir(iii) reductive elimination enables construction of seven-membered-ring sulfoxides.

Chemical science

Yang W, Li Y, Zhu J, Liu W, Ke J, He C.
PMID: 34094278
Chem Sci. 2020 Sep 03;11(37):10149-10158. doi: 10.1039/d0sc04180g.

Iridium has played an important role in the evolution of C-H activation chemistry over the last half century owing to its high reactivity towards stoichiometric C-H bond cleavage; however, the use of Ir(iii) complexes in catalytic C-H functionalization/C-C bond...

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Yang W, Li Y, Zhu J, et al. Lewis acid-assisted Ir(iii) reductive elimination enables construction of seven-membered-ring sulfoxides. Chem Sci. 2020;11(37):10149-10158doi: 10.1039/d0sc04180g.
Yang, W., Li, Y., Zhu, J., Liu, W., Ke, J., & He, C. (2020). Lewis acid-assisted Ir(iii) reductive elimination enables construction of seven-membered-ring sulfoxides. Chemical science, 11(37), 10149-10158. https://doi.org/10.1039/d0sc04180g
Yang, Wu, et al. "Lewis acid-assisted Ir(iii) reductive elimination enables construction of seven-membered-ring sulfoxides." Chemical science vol. 11,37 (2020): 10149-10158. doi: https://doi.org/10.1039/d0sc04180g
Yang W, Li Y, Zhu J, Liu W, Ke J, He C. Lewis acid-assisted Ir(iii) reductive elimination enables construction of seven-membered-ring sulfoxides. Chem Sci. 2020 Sep 03;11(37):10149-10158. doi: 10.1039/d0sc04180g. PMID: 34094278; PMCID: PMC8162422.
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A DFT examination of the role of proximal boron functionalities in the .

Organic & biomolecular chemistry

Durant AG, Nicol EA, McInnes BM, Schwan AL.
PMID: 34942637
Org Biomol Chem. 2021 Dec 23; doi: 10.1039/d1ob02083h. Epub 2021 Dec 23.

Sulfenic acid anions represent an emerging nucleophile for the preparation of sulfoxides. Their S-functionalization chemistry can often be influenced by a nearby group that interacts with the component atoms of the sulfenate through non-bonding interactions. This study uses DFT...

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Durant AG, Nicol EA, McInnes BM, et al. A DFT examination of the role of proximal boron functionalities in the . Org Biomol Chem. 2021;doi: 10.1039/d1ob02083h.
Durant, A. G., Nicol, E. A., McInnes, B. M., & Schwan, A. L. (2021). A DFT examination of the role of proximal boron functionalities in the . Organic & biomolecular chemistry, . https://doi.org/10.1039/d1ob02083h
Durant, Andrew G, et al. "A DFT examination of the role of proximal boron functionalities in the ." Organic & biomolecular chemistry vol. (2021). doi: https://doi.org/10.1039/d1ob02083h
Durant AG, Nicol EA, McInnes BM, Schwan AL. A DFT examination of the role of proximal boron functionalities in the . Org Biomol Chem. 2021 Dec 23; doi: 10.1039/d1ob02083h. Epub 2021 Dec 23. PMID: 34942637.
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Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides.

Organic & biomolecular chemistry

Sun M, Wang Z, Wang J, Guo P, Chen X, Li YM.
PMID: 27801460
Org Biomol Chem. 2016 Dec 07;14(45):10585-10588. doi: 10.1039/c6ob02040b. Epub 2016 Nov 01.

A palladium catalyzed efficient strategy for regio-selective ortho-arylation of sulfoxides with benzoyl peroxides via decarboxylation has been developed. This reaction proceeds smoothly, tolerates a variety of functional groups, and provides easy access to the synthesis of different biaryl compounds.

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Sun M, Wang Z, Wang J, et al. Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides. Org Biomol Chem. 2016;14(45):10585-10588doi: 10.1039/c6ob02040b.
Sun, M., Wang, Z., Wang, J., Guo, P., Chen, X., & Li, Y. M. (2016). Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides. Organic & biomolecular chemistry, 14(45), 10585-10588. https://doi.org/10.1039/c6ob02040b
Sun, Meng, et al. "Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides." Organic & biomolecular chemistry vol. 14,45 (2016): 10585-10588. doi: https://doi.org/10.1039/c6ob02040b
Sun M, Wang Z, Wang J, Guo P, Chen X, Li YM. Palladium-catalyzed decarboxylative ortho-arylation of 2-pyridyl sulfoxides with benzoyl peroxides. Org Biomol Chem. 2016 Dec 07;14(45):10585-10588. doi: 10.1039/c6ob02040b. Epub 2016 Nov 01. PMID: 27801460.
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Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes.

Organic letters

Frutos M, Ortuño MA, Lledos A, Viso A, Fernández de la Pradilla R, de la Torre MC, Sierra MA, Gornitzka H, Hemmert C.
PMID: 28135109
Org Lett. 2017 Feb 17;19(4):822-825. doi: 10.1021/acs.orglett.6b03808. Epub 2017 Jan 30.

New and well-characterized Ag-bis(1,2,3-triazolylidene) complexes having enantiopure (S)-sulfoxides upon sequential treatment with alcohols and Au(I) form separable mixtures of regioisomeric C-unsubstituted Au-1,2,3-triazolylidene complexes. Mechanistic studies and DFT calculations support a desulfinylation process for in situ generated free triazolylidene salts.

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Frutos M, Ortuño MA, Lledos A, et al. Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes. Org Lett. 2017;19(4):822-825doi: 10.1021/acs.orglett.6b03808.
Frutos, M., Ortuño, M. A., Lledos, A., Viso, A., Fernández de la Pradilla, R., de la Torre, M. C., Sierra, M. A., Gornitzka, H., & Hemmert, C. (2017). Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes. Organic letters, 19(4), 822-825. https://doi.org/10.1021/acs.orglett.6b03808
Frutos, María, et al. "Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes." Organic letters vol. 19,4 (2017): 822-825. doi: https://doi.org/10.1021/acs.orglett.6b03808
Frutos M, Ortuño MA, Lledos A, Viso A, Fernández de la Pradilla R, de la Torre MC, Sierra MA, Gornitzka H, Hemmert C. Desulfinylation of Ag(I) Sulfinyl Mesoionic Carbenes: Preparation of C-Unsubstituted Au(I)-1,2,3-Triazole Carbene Complexes. Org Lett. 2017 Feb 17;19(4):822-825. doi: 10.1021/acs.orglett.6b03808. Epub 2017 Jan 30. PMID: 28135109.
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α-Carbonyl Cations in Sulfoxide-Driven Oxidative Cyclizations.

Angewandte Chemie (International ed. in English)

Stopka T, Niggemann M, Maulide N.
PMID: 28834106
Angew Chem Int Ed Engl. 2017 Oct 16;56(43):13270-13274. doi: 10.1002/anie.201705964. Epub 2017 Sep 25.

The selective, metal-free generation of α-carbonyl cations from simple internal alkynes was accomplished by the addition of a sulfoxide to a densely substituted vinyl cation. The high reactivity of the α-carbonyl cations was found to efficiently induce hydrogen and...

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Stopka T, Niggemann M, Maulide N. α-Carbonyl Cations in Sulfoxide-Driven Oxidative Cyclizations. Angew Chem Int Ed Engl. 2017;56(43):13270-13274doi: 10.1002/anie.201705964.
Stopka, T., Niggemann, M., & Maulide, N. (2017). α-Carbonyl Cations in Sulfoxide-Driven Oxidative Cyclizations. Angewandte Chemie (International ed. in English), 56(43), 13270-13274. https://doi.org/10.1002/anie.201705964
Stopka, Tobias, et al. "α-Carbonyl Cations in Sulfoxide-Driven Oxidative Cyclizations." Angewandte Chemie (International ed. in English) vol. 56,43 (2017): 13270-13274. doi: https://doi.org/10.1002/anie.201705964
Stopka T, Niggemann M, Maulide N. α-Carbonyl Cations in Sulfoxide-Driven Oxidative Cyclizations. Angew Chem Int Ed Engl. 2017 Oct 16;56(43):13270-13274. doi: 10.1002/anie.201705964. Epub 2017 Sep 25. PMID: 28834106.
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Analysis of Methionine Oxidation in Myosin Isoforms in Porcine Skeletal Muscle by LC-MS/MS Analysis.

Korean journal for food science of animal resources

Jeong JY, Jung EY, Jeong TC, Yang HS, Kim GD.
PMID: 27194935
Korean J Food Sci Anim Resour. 2016;36(2):254-61. doi: 10.5851/kosfa.2016.36.2.254. Epub 2016 Apr 30.

The purpose of this study was to analyze oxidized methionines in the myosin isoforms of porcine longissimus thoracis, psoas major, and semimembranosus muscles by liquid chromatography (LC) and mass spectrometry (MS). A total of 836 queries matched to four...

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Jeong JY, Jung EY, Jeong TC, et al. Analysis of Methionine Oxidation in Myosin Isoforms in Porcine Skeletal Muscle by LC-MS/MS Analysis. Korean J Food Sci Anim Resour. 2016;36(2):254-61doi: 10.5851/kosfa.2016.36.2.254.
Jeong, J. Y., Jung, E. Y., Jeong, T. C., Yang, H. S., & Kim, G. D. (2016). Analysis of Methionine Oxidation in Myosin Isoforms in Porcine Skeletal Muscle by LC-MS/MS Analysis. Korean journal for food science of animal resources, 36(2), 254-61. https://doi.org/10.5851/kosfa.2016.36.2.254
Jeong, Jin-Yeon, et al. "Analysis of Methionine Oxidation in Myosin Isoforms in Porcine Skeletal Muscle by LC-MS/MS Analysis." Korean journal for food science of animal resources vol. 36,2 (2016): 254-61. doi: https://doi.org/10.5851/kosfa.2016.36.2.254
Jeong JY, Jung EY, Jeong TC, Yang HS, Kim GD. Analysis of Methionine Oxidation in Myosin Isoforms in Porcine Skeletal Muscle by LC-MS/MS Analysis. Korean J Food Sci Anim Resour. 2016;36(2):254-61. doi: 10.5851/kosfa.2016.36.2.254. Epub 2016 Apr 30. PMID: 27194935; PMCID: PMC4869553.
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Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening.

Crystal growth & design

Engwerda AHJ, Koning N, Tinnemans P, Meekes H, Bickelhaupt FM, Rutjes FPJT, Vlieg E.
PMID: 28794692
Cryst Growth Des. 2017 Aug 02;17(8):4454-4457. doi: 10.1021/acs.cgd.7b00828. Epub 2017 Jul 03.

Despite the importance of enantiopure chiral sulfoxides, few methods exist that allow for their deracemization. Here, we show that an enantiopure sulfoxide can be produced from the corresponding racemate using Viedma ripening involving rearrangement-induced racemization. The suitable candidate for...

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Engwerda AHJ, Koning N, Tinnemans P, et al. Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening. Cryst Growth Des. 2017;17(8):4454-4457doi: 10.1021/acs.cgd.7b00828.
Engwerda, A. H. J., Koning, N., Tinnemans, P., Meekes, H., Bickelhaupt, F. M., Rutjes, F. P. J. T., & Vlieg, E. (2017). Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening. Crystal growth & design, 17(8), 4454-4457. https://doi.org/10.1021/acs.cgd.7b00828
Engwerda, Anthonius H J, et al. "Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening." Crystal growth & design vol. 17,8 (2017): 4454-4457. doi: https://doi.org/10.1021/acs.cgd.7b00828
Engwerda AHJ, Koning N, Tinnemans P, Meekes H, Bickelhaupt FM, Rutjes FPJT, Vlieg E. Deracemization of a Racemic Allylic Sulfoxide Using Viedma Ripening. Cryst Growth Des. 2017 Aug 02;17(8):4454-4457. doi: 10.1021/acs.cgd.7b00828. Epub 2017 Jul 03. PMID: 28794692; PMCID: PMC5543398.
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