Selective mono-arylation in palladium-catalyzed cross-coupling reaction of dichlorotriazines with phenylboronate ester derivatives

Dong, Jin-Fu; Yu, Xin; Ning, Chengqing; Hu, Liang; Nabetani, Yu

doi:10.1016/j.cclet.2012.12.004

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Cited by 6 publications

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A Sequential Suzuki Coupling Approach to Unsymmetrical Aryl s‐Triazines from Cyanuric Chloride

et al. 2017

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A practical approach has been developed for efficient synthesis of unsymmetrical aryl striazines via highly selective sequential Suzuki coupling of cyanuric chloride (2,4,6-trichlorotriazine) with aryl or vinyl boronic or diarylborinic acids catalysed by 0.1-0.5 mol% Pd(PPh 3 ) 2 Cl 2 under mild conditions. The second and third Suzuki couplings for unsymmetrically trisubstituted aryl striazines could be more practically conducted in one-pot procedure. An electron-withdrawing conjugate group at phenyl ring of arylboronic acids was unexpectedly found to completely block the coupling while steric hindrance from an ortho electrondonating substituent could be overcome.

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