Research
(1)
Transfer (de)hydration catalysis
Water is an ideal reagent for the economical synthesis of oxygen-containing organic compounds. Selective organic synthesis using water as a reagent is often not trivial because conventional hydrolysis/hydration requires harsh reaction conditions. This difficulty lies on two factors: 1) many organic compounds are poorly soluble in water, 2) catalysts that can effectively activate substrate/water under aqueous conditions are often lacking. In order to address these issues, we focused on "catalytic transfer hydration" strategy, the formal metal-catalyzed hydration/hydrolysis of unsaturated molecules (e.g. nitriles) using H₂O donors (e.g. amides). The reverse strategy, "catalytic transfer dehydration", is also effective in dehydrating organic molecules (e.g. amides) using H₂O acceptors under aqueous conditions.
Water is an ideal reagent for the economical synthesis of oxygen-containing organic compounds. Selective organic synthesis using water as a reagent is often not trivial because conventional hydrolysis/hydration requires harsh reaction conditions. This difficulty lies on two factors: 1) many organic compounds are poorly soluble in water, 2) catalysts that can effectively activate substrate/water under aqueous conditions are often lacking. In order to address these issues, we focused on "catalytic transfer hydration" strategy, the formal metal-catalyzed hydration/hydrolysis of unsaturated molecules (e.g. nitriles) using H₂O donors (e.g. amides). The reverse strategy, "catalytic transfer dehydration", is also effective in dehydrating organic molecules (e.g. amides) using H₂O acceptors under aqueous conditions.
Review: Tetrahedron Lett. 2020, 61, 151557; J. Org. Synth. Chem. Jpn. 2024, 82, 14 (in Japanese).
Hydration: J. Am. Chem. Soc. 2019, 141, 825; Synlett 2019, 30, 1977; Dehydration: Org. Lett. 2019, 21, 4767.
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(2)
Effective deuteration of materials: Deut-Switch
Deuterium (D) is a non-radioactive, stable isotope of hydrogen. Most properties of protium and deuterium are similar; however, there are major physical differences between the two isotopes which make their substitution with one another an interesting research field. They are: (1) D is twice as heavy as protium and (2) C−D bonds are stronger than C−H bonds. As a result, deuterated materials occasionally show quite different properties in comparison with their non-deuterated analogs. Deuterium-control (isotope-control) on the material properties is an emerging yet immature concept in material design worldwide. We focus on clarifying the impact of deuteration in molecular material design aided by selective catalytic deuteration technologies. We wish to propose a new material design concept "Deut-Switch", which aims to maximize the material functions by precise and logical deuteration of materials and accurate prediction of the isotopic effect.
Deuteration of Alcohols. Chem. Sci. 2022, 13, 8744; Deuterated Organocatalysts. Tetrahedron Lett. 2022, 96, 153753; Chem. Eur. J. 2023, 29, e202301866; Bull. Chem. Soc. Jpn. 2024, 97, uoae028.
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