N-methyl-4-bromobenzothiazolium triflate | 1341198-69-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机磺酸及其衍生物
• 英文名称: N-methyl-4-bromobenzothiazolium triflate
• 英文别名: N-methyl-4-bromothiazolium triflate
• CAS: 1341198-69-3
• 化学式: CF₃O₃S*C₄H₅BrNS
• 分子量: 328.131
• InChiKey: CQCNOZMXDKQYRD-UHFFFAOYSA-M

计算性质

• 辛醇/水分配系数(LogP)：
  1.39
• 重原子数：
  15.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  61.08
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  四(三苯基膦)钯 、 N-methyl-4-bromobenzothiazolium triflate 以 甲苯 为溶剂， 以93.5%的产率得到trans-bromo(N-methyl-3,4-dihydrothiazol-4-ylidene)bis(triphenylphosphine)palladium(II) triflate
  参考文献：
  名称：

  Normal and abnormal carbene complexes derived from thiazole: Preparation and a preliminary investigation of their relative catalytic performance

  摘要：

  Readily prepared 2-, 4- and 5-bromo-3-methyl thiazolium triflates react by oxidative substitution with M(PPh3)(4) (M = Ni or Pd) to furnish five of the expected normal and abnormal cationic thiazolylidene complexes (1a, 1b, 2a, 2b, and 3b). Carbene complex formation is accompanied by a ca. 40 ppm downfield shift of the alpha-N carbene carbons in Pd complexes 1 and 2 in their C-13 NMR spectra but the chemical shift of C(carbene) in the abnormal 3b (delta 135.7) is particularly low. Crystal and molecular structures of complexes 1a, 2b, and 3b all indicate a square planar arrangement of the ligands around the central metal atoms. The new complexes catalyse Suzuki-Miyaura aryl coupling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.07.028
• 作为产物：
  描述：

  4-溴噻唑 、 三氟甲烷磺酸甲酯 以 二氯甲烷 为溶剂， 反应 17.0h， 以95.9%的产率得到N-methyl-4-bromobenzothiazolium triflate
  参考文献：
  名称：

  Normal and abnormal carbene complexes derived from thiazole: Preparation and a preliminary investigation of their relative catalytic performance

  摘要：

  Readily prepared 2-, 4- and 5-bromo-3-methyl thiazolium triflates react by oxidative substitution with M(PPh3)(4) (M = Ni or Pd) to furnish five of the expected normal and abnormal cationic thiazolylidene complexes (1a, 1b, 2a, 2b, and 3b). Carbene complex formation is accompanied by a ca. 40 ppm downfield shift of the alpha-N carbene carbons in Pd complexes 1 and 2 in their C-13 NMR spectra but the chemical shift of C(carbene) in the abnormal 3b (delta 135.7) is particularly low. Crystal and molecular structures of complexes 1a, 2b, and 3b all indicate a square planar arrangement of the ligands around the central metal atoms. The new complexes catalyse Suzuki-Miyaura aryl coupling. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.poly.2011.07.028