potassium (2,5-dimethoxyphenyl)trifluoroborate

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: potassium (2,5-dimethoxyphenyl)trifluoroborate
• 英文别名: potassium;(2,5-dimethoxyphenyl)-trifluoroboranuide
• 化学式: C₈H₉BF₃O₂*K
• 分子量: 244.063
• InChiKey: AVAZYGWIAYOXAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.24
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  18.5
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  potassium (2,5-dimethoxyphenyl)trifluoroborate 在 aluminum oxide 、 水 作用下， 反应 0.25h， 以87%的产率得到2,5-二甲氧基苯硼酸
  参考文献：
  名称：

  Thermal and microwave hydrolysis of organotrifluoroborates mediated by alumina

  摘要：

  Hydrolysis of organotrifluoroborates to the corresponding organoboronic acids is readily achieved under either thermal or microwave conditions in the presence of alumina. The organoboronic acid products are obtained in good to excellent yields with essentially no loss of boronated reagent due to protoboronation. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2009.09.008
• 作为产物：
  描述：

  2,5-二甲氧基苯硼酸 在 二氟化氢钾 作用下， 以 甲醇 、 水 为溶剂， 以83%的产率得到potassium (2,5-dimethoxyphenyl)trifluoroborate
  参考文献：
  名称：

  Nickel-Catalyzed Cross-Coupling of Potassium Aryl- and Heteroaryltrifluoroborates with Unactivated Alkyl Halides

  摘要：

  A method for the cross-coupling of alkyl electrophiles with various potassium aryl- and heteroaryltrifluoroborates has been developed. Nearly stoichiometric amounts of organoboron species could be employed to cross-couple a large variety of challenging heteroaryl nucleophiles. Several functional groups were tolerated on both the electrophilic and the nucleophilic partners. Chemoselective reactivity of C(sp(3))-Br bonds in the presence of C(sp(2))-Br bonds was achieved.

  DOI：

  10.1021/ol102717x

文献信息

• Halodeboronation of organotrifluoroborates using tetrabutylammonium tribromide or cesium triiodide
  作者：Min-Liang Yao、George W. Kabalka、David W. Blevins、Marepally Srinivasa Reddy、Li Yong

  DOI：10.1016/j.tet.2012.03.016

  日期：2012.5

  Halodeboronation of organotrifluoroborates using commercially available tetrabutylammonium tribromide (TBATB) or cesium triiodide in aqueous medium is reported. The mild, transition metal-free method has proven to be tolerant of a wide range of functional groups. High regio- and chemoselectivity are observed. Two synthetic routes to (Z)-dibromoalkenes from alkynes, through stereodefined (Z)-2-brom

  报道了在水介质中使用市售的三溴化四丁基铵（TBATB）或三碘化铯对有机三氟硼酸盐进行卤代硼烷化。事实证明，这种温和的不含过渡金属的方法可耐受多种官能团。观察到高的区域选择性和化学选择性。两个合成路线（ż）从炔-dibromoalkenes，通过stereodefined（ż）-2- bromoalkenyltrifluoroborates和（Ž）-1,2-双（硼烷基）alkenyltrifluoroborates，已经使用TBATB介导bromodeboronation作为关键步骤开发的。
• Arylation and Heteroarylation of Thienylsulfonamides with Organotrifluoroborates
  作者：Mnaza Noreen、Nasir Rasool、Mirna El Khatib、Gary A. Molander

  DOI：10.1021/jo501323z

  日期：2014.8.1

  the Suzuki cross-coupling of unprotected thienylsulfonamides from air- and bench-stable organotrifluoroborates in the absence of a protecting group on the sulfonamide nitrogen. The developed synthetic method can be applied to the preparation of various arylated and heteroarylated thienylsulfonamides under conditions that are tolerant of a broad range of functional groups.

  在磺酰胺氮上没有保护基团的情况下，已经开发了一种温和、实用的方案，用于将未受保护的噻吩磺酰胺与空气和台式稳定的有机三氟硼酸盐进行 Suzuki 交叉偶联。所开发的合成方法可用于在耐受广泛官能团的条件下制备各种芳基化和杂芳基化噻吩磺酰胺。
• Oxidative Cross-Coupling of Boron and Antimony Nucleophiles via Palladium(I)
  作者：Quillon Simpson、Matthew J. G. Sinclair、David W. Lupton、Adrian B. Chaplin、Joel F. Hooper

  DOI：10.1021/acs.orglett.8b01989

  日期：2018.9.21

  The use of an isolatable, monomeric Pd(I) complex as a catalyst for the oxidative cross-coupling of aryl-antimony and aryl-boron nucleophiles is reported. This reaction tolerates a wide variety of substrates, with >20:1 selectivity for cross-coupled products. This strategy offers a new approach to achieving the selective cross-coupling of nucleophiles.

  据报道，可分离的单体Pd（I）配合物用作芳基-锑和芳基-硼亲核试剂的氧化交叉偶联的催化剂。该反应可耐受多种底物，对交叉偶联产物的选择性> 20：1。该策略提供了一种实现亲核试剂选择性交叉偶联的新方法。
• Chemoselective Bromodeboronation of Organotrifluoroborates Using Tetrabutylammonium Tribromide: Application in (<i>Z</i>)-Dibromoalkene Syntheses
  作者：Min-Liang Yao、Marepally Srinivasa Reddy、Li Yong、Ingrid Walfish、David W. Blevins、George W. Kabalka

  DOI：10.1021/ol9027144

  日期：2010.2.19

  Tetrabutylammonium tribromide (TBATB) has been found to be a unique bromodeboronation reagent for organotrifluoroborates. When compared to previously reported bromodeboronation methods, the mild and metal-free reaction conditions tolerate a wider range of functional groups. High regio- and chemoselectivity are observed in the presence of both unsaturated carbon-carbon bonds and aldehyde functional groups. An efficient synthetic route to (Z)-dibromoalkenes from terminal alkynes has been developed using the TBATB-mediated bromodeboronation as a key step.
• Thermal and microwave hydrolysis of organotrifluoroborates mediated by alumina
  作者：George W. Kabalka、Vitali Coltuclu

  DOI：10.1016/j.tetlet.2009.09.008

  日期：2009.11

  Hydrolysis of organotrifluoroborates to the corresponding organoboronic acids is readily achieved under either thermal or microwave conditions in the presence of alumina. The organoboronic acid products are obtained in good to excellent yields with essentially no loss of boronated reagent due to protoboronation. (C) 2009 Elsevier Ltd. All rights reserved.