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

Shotaro Izawa, Hidefumi Nakatsuji, Yoo Tanabe
2018 Molbank  
Cyclo-condensation of N-methyl-2-bromoaniline with chlorocarbonylsulfenyl chloride (CCSC) promoted by PhNMe 2 and AlCl 3 , 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) 2 B 2 ] produced a novel N-methyl-4-(pin)B-2(3H)-benzothiazol-2-one (3) using (pin) 2 B 2 in the presence of the PdCl 2 (PPh 3 ) 2 catalyst. The obtained 4-(pin)B compound is regarded as a new entry
more » ... rded as a new entry for the library of Suzuki-Miyaura cross-coupling reactions. 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.
doi:10.3390/m976 fatcat:qnwlqgy6o5eyxbmclhrvuynhiy