Exploiting 1,1-Dibromoalkenes as Direct Precursors to 5-Substituted 1,2,3-Triazoles.

Keywords: triazoles; nitrogen heterocycles; acetylides; regioselectivity; one-pot EN triazoles nitrogen heterocycles acetylides regioselectivity one-pot 3862 3874 13 11/01/23 20231116 NES 231116 Graph The 1,2,3-triazole is a valuable motif, used extensively across all areas of chemical sciences. SP 1 sp H NMR (500 MHz, 25.0 °C, CDCl SB 3 sb ): = 7.72 (s, 1 H, triazole), 7.31-7.27 (m, 3 H, Ar), 7.22-7.18 (m, 2 H, Ar), 7.12-7.08 (m, 2 H, Ar), 7.07-7.04 (m, 2 H, Ar), 5.52 (s, 2 H, CH SB 2 sb ). SP 13 sp C{ SP 1 sp H} NMR (126 MHz, 25.0 °C, CDCl SB 3 sb ): = 145.5 (triazole CH), 136.1 (Ph), 131.5 (triazole C5), 128.7 (2 × PhH), 127.8 (PhH), 126.3 (2 × PhH), 52.8 (CH SB 2 sb ), 30.2 ( I t i Bu), 29.8 (3 × CH SB 3 sb ). SP 1 sp H NMR (400 MHz, 26.8 °C, CDCl SB 3 sb ): = 7.95 (d, I J i = 8.5 Hz, 2 H, Ts Ar), 7.39-7.35 (m, 3 H, Ts Ar & triazole), 2.82 (dd, I J i = 6.9, 0.7 Hz, 2 H, I i i Bu), 2.44 (s, 3 H, Ts CH SB 3 sb ), 2.01 (tsept, I J i = 6.9, 6.7 Hz, 1 H, I i i Bu), 0.96 (d, I J i = 6.7 Hz, 6 H, I i i Bu). [Extracted from the article]