A Practical Method to Stereospecifically Synthesize trans‐Stilbene Derivatives

Abstract

A practical method to stereospecifically synthesize trans-stilbenes was developed via the one-pot benzylation-dehydration reaction of aromatic aldehydes with benzyltrimethylsilane (BTMS), which was driven by tetrabutylammonium fluoride (TBAF) in THF. At the same time a plausible description of the whole process was proposed and the effects of substituted groups on the reaction were investigated. Also this method was employed to synthesize three precursors of natural products with excellent yields, which demonstrated that this method is much efficient and practical in the synthesis of some natural products.

Late-Stage Derivatization of Buflavine by Nickel-Catalyzed Direct Substitution of a Methoxy Group via C–O Bond Activation

“…13 C NMR (101 MHz, CDCl 3 ):  = 157. 0, 156.4, 143.8, 143.7, 143.5, 143.4, 141.3, 141.1, 141.0, 140.3, 140.2, 140.0, 139.5, 137.3, 134.3, 133.0, 132.6, 132.4, 131.2, 131.11, 131.07, 129.4, 129.3, 129.1, 128.9, 128.8, 128.1, 127.8, 127.7, 127.5, 127.5, 126.0, 125.7, 125.4, 125.1, 125.0, 120.9, 120.80, 120.75, 120.7, 112.6, 111.2, 111.1, 73.54, 73.45, 73.2, 58.72, 58.66, 58.6, 58.4, 58.3, 57.5, 57.3, 55.50, 55.47, 46.0, 45.3, 44.8, 40.9, 40.8, 32.6, 32.5, 32.1, 32.0. MS: m/z (%) = 453 (M + +2, 19), 452 (16), 451 (M + , 21), 438 (19), 436 (19), 267 (27), 266 (44), 252 (26), 236 (11), 225 (12), 224 (58), 223 (100), 222 (11), 209 (20), 194 (10), 193 (45), 191 (14)…”

“…1 H NMR (400 MHz, CDCl 3 ):  = 7.61-7.56 (m, 5 H), 7.45-7.24 (m, 15 H), 7.01 (s, 1 H), 6.91 (s, 1 H), 3.90 (s, 3 H), 3.83 (s, 3 H), 3.62 (t, J = 12.6 Hz, 2 H), 3.32-3.25 (m, 2 H), 3.16 (dd, J = 13.5, 1.2 Hz, 2 H), 2.65-2.50 (m, 9 H), 2.47 (s, 3 H). 13 C NMR (101 MHz, CDCl 3 ):  = 155.9, 155.3, 141.4, 141.2, 140.9, 140.1, 139.7, 138.1, 137.9, 133.7, 133.2, 131.8, 129.8, 129.7, 129.54, 129.51, 129.4, 129.2, 129.1, 128.2, 127.98, 127.96, 127.8, 127.0, 126.1, 113.3, 112.0, 58.9, 58.8, 58.4, 57.5, 55.7, 55.6, 46.2, 44.9, 32.8, 32.1. MS: m/z (%) = 330 (11), 329 (M + , 43), 328 (21), 314 (23), 287 (25), 286 (100), 285 (31), 271 (20), 270 (17), 256 (14), 255 (37), 254 (12), 253 (21), 252 (31), 241 (14), 240 (11), 239 (18), 209 (10), 165 (15), 119 (11), 115 (16), 91 (16), 42 (14).…”

“…13 C NMR (101 MHz, CDCl 3 ):  = 156. 40, 155.82, 141.26, 141.21, 140.04, 139.72, 138.30, 136.50, 135.87, 134.87, 133.24, 132.81, 129.83, 129.76, 129.56, 129.43, 129.27, 129.15, 128.90, 128.70, 128.28, 127.93, 127.77, 127.65, 127.30, 126.13, 125.32, 125.04, 123.58, 113.13, 111.69, 60.38, 58.82, 58.65, 58.49, 57.65, 55.60, 45.91, 45.34, 32.58, 32. (14), 358 (22), 349 (10), 348 (35), 347 (28), 346 (100), 305 (14), 303 (37), 296 (10), 281 (16), 278 (13), 268 (34), 267 (26), 266 (12), 265 (23), 253 (28), 252 (26), 221 (11), 219 (10), 208 (11), 207 (27), 193 (11), 191 (30), 165 (11), 147 (11), 140 (15), 139 (13), 138 (15), 132 (22), 131 (14), 127 (13), 126 (27), 125 (30), 73 (16)…”