About the Research
Research Theme
Synthesis and application of functional organic molecules
Keyword
Research Outline
As a group focusing on functional organic chemistry, we will be working on the following two areas: (1) development of new synthetic methodologies using modern techniques in organic synthesis and transition metal catalysis, and (2) preparation of photoresponsive molecules and the study of their functions. In particular, we will work collaboratively with other research groups to implement approaches in theoretical calculations as well as machine learning to faciliate the molecular design and mechanistic understanding.
Research History
Please see CV (updated August 2022).
For details on MANABIYA course topics, please follow this link. To learn more about MANABIYA in general, please click here.
Representative Research Achievements
N,N’-Disubstituted Indigos as Readily Available Red-Light Photoswitches with Tunable Thermal Half-Lives. C.-Y. Huang, A. Bonasera, L. Hristov, Y. Garmshausen, B. M. Schmidt, D. Jacquemin, S. Hecht, J. Am. Chem. Soc., 2017, 139, 15205–15211.
DOI: 10.1021/jacs.7b08726
Nickel-Catalyzed Enantioselective Reductive Cross-Coupling of Styrenyl Aziridines. B. P. Woods, M. Orlandi, C.-Y. Huang, M. S. Sigman, A. G. Doyle, J. Am. Chem. Soc., 2017, 139, 5688–5691. DOI: 10.1021/jacs.7b03448
Electron-Deficient Olefin Ligands Enable Generation of Quaternary Carbons by Ni-Catalyzed Cross-Coupling. C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc., 2015, 137, 5638–5641.
DOI: 10.1021/jacs.5b02503
The Chemistry of Transition Metals with Three-Membered Ring Heterocycles. C.-Y. Huang, A. G. Doyle, Chem. Rev., 2014, 114, 8153–8198. DOI: 10.1021/cr500036t
Nickel-Catalyzed Negishi Alkylations of Styrenyl Aziridines. C.-Y. Huang, A. G. Doyle, J. Am. Chem. Soc., 2012, 134, 9541–9544. DOI: 10.1021/ja3013825
Related Research
- Defluorinative C‒O Coupling between Trifluoromethylarenes and Alcohols via Copper Photoredox Catalysis
- Mechanistic Exploration of N-Heterocyclic Carbene Boranes as the Hydrogen Atom Transfer Reagent in Selective Hydrodefluorination Reactions
- New avenue towards widely applicable indigo photoswitches – Combining experimental, computational and data-science approaches –
- Indigo dye derivatives show efficient red-light photoswitching in the solid state
Publications
2024
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Mechanistic Exploration of N-Heterocyclic Carbene Boranes as the Hydrogen Atom Transfer Reagent in Selective Hydrodefluorination Reactions
, B. Skjelstad, S. Maeda, D. Huang, Acs Catalysis, 2024, 14, 17547–17555
DOI: 10.1021/acscatal.4c05092
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Accessing a Diverse Set of Functional Red-Light Photoswitches by Selective Copper-Catalyzed Indigo N-Arylation
, P. Saha, J. Jiang, K. Suzuki, A. Jasny, B. Schmidt, S. Maeda, S. Hecht, C. Huang, J. Am. Chem. Soc., 2024, 146, 31, 21367-21376
DOI: 10.1021/jacs.4c03543
2023
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Direct a-Trifluoromethylthiolation of Carboxylic Acids Enabled by Boron Catalysis
, C. Y. D. Huang, M. Sawamura, Y. Shimizu, Synlett, 2023, ,
DOI: 10.1055/a-2071-4465
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A Blueprint for Transforming Indigos to Photoresponsive Molecular Tools
, S. Hecht, Chem. Eur. J., 2023, ,
DOI: 10.1002/chem.202300981
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Red-Light Photoswitching of Indigos in Polymer Thin Films
, J. Viljakka, M. Virkki, C. Y. Huang, S. Hecht, A. Priimagi, Chem. Sci., 2023, ,
DOI: 10.1039/d2sc06790k
2022
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Mechanistic Insights into the Photoisomerization of N,N '-Disubstituted Indigos
, J. Jovaisaite, C. Y. Huang, P. Baronas, K. Tulaite, S. Jursenas, D. Jacquemin, S. Hecht, Chem. Eur. J., 2022, 28,
DOI: 10.1002/chem.202200496