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Iwamoto T, Hosokawa A, Nakamura M. Endergonic addition of N-methylamines to aromatic ketones driven by photochemical offset of the entropic cost. Chem Commun (Camb). 2019;55(78):11683-11686doi: 10.1039/c9cc06011a.
Iwamoto, T., Hosokawa, A., & Nakamura, M. (2019). Endergonic addition of N-methylamines to aromatic ketones driven by photochemical offset of the entropic cost. Chemical communications (Cambridge, England), 55(78), 11683-11686. https://doi.org/10.1039/c9cc06011a
Iwamoto, Takahiro, et al. "Endergonic addition of N-methylamines to aromatic ketones driven by photochemical offset of the entropic cost." Chemical communications (Cambridge, England) vol. 55,78 (2019): 11683-11686. doi: https://doi.org/10.1039/c9cc06011a
Iwamoto T, Hosokawa A, Nakamura M. Endergonic addition of N-methylamines to aromatic ketones driven by photochemical offset of the entropic cost. Chem Commun (Camb). 2019 Oct 07;55(78):11683-11686. doi: 10.1039/c9cc06011a. Epub 2019 Sep 12. PMID: 31513188.
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Chem Commun (Camb). 2019 Oct 07;55(78):11683-11686. doi: 10.1039/c9cc06011a. Epub 2019 Sep 12.

Endergonic addition of N-methylamines to aromatic ketones driven by photochemical offset of the entropic cost.

Chemical communications (Cambridge, England)

Takahiro Iwamoto, Atsushi Hosokawa, Masaharu Nakamura

Affiliations

  1. Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan. [email protected] [email protected] and Department of Energy and Hydrocarbon Chemistry, Graduate School of Engineering, Kyoto University, Kyoto 615-8510, Japan.

PMID: 31513188 DOI: 10.1039/c9cc06011a

Abstract

Intermolecular addition reactions are generally accompanied by an entropic penalty due to the decrease of molecular numbers during the reaction, which sometimes makes the reaction endergonic. Here we demonstrate that such an endergonic reaction can be promoted with light-energy as a driving force; N-methylamines were added to aromatic ketones to produce aminoalcohols under UV-light irradiation. The reaction represents an obvious example showing that the photochemical approach is effective to offset such an entropic cost, and thereby to drive thermodynamically uphill addition reactions. Moreover the present reactions are highly expedient from the synthetic view point, being transition-metal-catalyst-free, scalable, highly atom economical, and regioselective. The product amines can be converted in one step to functional multi-arylated enamines, which are potentially valuable compounds in electronic materials.

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