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Molbank 2018, 2018(1), M976; https://doi.org/10.3390/M976

Straightforward Synthesis of N-Methyl-4-(pin)B-2(3H)-benzothiazol-2-one: A Promising Cross-Coupling Reagent

Department of Chemistry, School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda, Hyogo 669-1337, Japan
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Received: 28 December 2017 / Revised: 16 January 2018 / Accepted: 18 January 2018 / Published: 23 January 2018
(This article belongs to the Special Issue Heterocycles)
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Abstract

Cyclo-condensation of N-methyl-2-bromoaniline with chlorocarbonylsulfenyl chloride (CCSC) promoted by PhNMe2 and AlCl3, afforded N-methyl-2-bromo-2(3H)-benzothiazol-2-one in good yield. Miyaura–Ishiyama cross-coupling of this brominated 2(3H)-benzothiazol-2-one with bis(pinacolato)diborone [(pin)2B2] produced a novel N-methyl-4-(pin)B-2(3H)-benzothiazol-2-one (3) using (pin)2B2 in the presence of the PdCl2(PPh3)2 catalyst. The obtained 4-(pin)B compound is regarded as a new entry for the library of Suzuki–Miyaura cross-coupling reactions. View Full-Text
Keywords: heterocycles; benzothiazol-2-ones; cyclo-condensation; chlorocarbonylsulfenyl chloride; S,N-containing heterocycles; 4-substituted N-methyl-2-bromo-2(3H)-benzothiazol-2-ones; cross-coupling reagent; Suzuki–Miyaura cross-coupling; Miyaura–Ishiyama cross-coupling heterocycles; benzothiazol-2-ones; cyclo-condensation; chlorocarbonylsulfenyl chloride; S,N-containing heterocycles; 4-substituted N-methyl-2-bromo-2(3H)-benzothiazol-2-ones; cross-coupling reagent; Suzuki–Miyaura cross-coupling; Miyaura–Ishiyama cross-coupling
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Izawa, S.; Nakatsuji, H.; Tanabe, Y. Straightforward Synthesis of N-Methyl-4-(pin)B-2(3H)-benzothiazol-2-one: A Promising Cross-Coupling Reagent. Molbank 2018, 2018, M976.

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