methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-2-carboxylate | 1227664-19-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-2-carboxylate
• 英文别名: Methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-benzofuran-2-carboxylate
• CAS: 1227664-19-8
• 化学式: C₁₆H₁₉BO₅
• 分子量: 302.135
• InChiKey: OOWMTFAJTZTXEA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.52
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  57.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯并呋喃-2-羧酸甲酯 、 联硼酸频那醇酯 在 (1,5-cyclooctadiene)(methoxy)iridium(I) dimer 作用下， 以 正己烷 为溶剂， 反应 1.0h， 以92%的产率得到methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzofuran-2-carboxylate
  参考文献：
  名称：

  Ester-Directed Regioselective Borylation of Heteroarenes Catalyzed by a Silica-Supported Iridium Complex

  摘要：

  The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene. pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.

  DOI：

  10.1021/jo100352b

文献信息

• Ester-Directed Regioselective Borylation of Heteroarenes Catalyzed by a Silica-Supported Iridium Complex
  作者：Soichiro Kawamorita、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/jo100352b

  日期：2010.6.4

  The ester-directed regioselective borylation of arenes catalyzed by a silica-supported monophosphine-Ir complex displayed a significantly broad substrate scope toward heteroaromatic compounds, including thiophene. pyrrole, furan, benzothiophene, benzofuran, indole, and carbazole derivatives. The regioselectivity is complementary to the selectivities observed in the heteroarene C-H borylation with the dtbpy-Ir catalyst system.
• N,B-Bidentate Boryl Ligand-Supported Iridium Catalyst for Efficient Functional-Group-Directed C–H Borylation
  作者：Guanghui Wang、Li Liu、Hong Wang、You-Song Ding、Jing Zhou、Shuai Mao、Pengfei Li

  DOI：10.1021/jacs.6b11867

  日期：2017.1.11

  Convenient silylborane precursors for introducing N,B-bidentate boryl ligands onto transition metals were designed, prepared, and employed in ready formation of irdium(III) complexes via Si-B oxidative addition. A practical, efficient catalytic ortho-borylation reaction of arenes with a broad range of directing groups was developed using an in situ generated catalyst from the silylborane preligand 3c and [IrCl(COD)](2).